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Wuhan Fortuna Chemical Co.,Ltd

Chemical Supplier 3-O-Benzyl-4-C-hydroxyMethyl-1,2-O-isopropylidene-alpha-D-ribofuranose Cas 63593-03-3 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine c

3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene-alpha-D-erythropentofuranose

Cas:63593-03-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

3-O-Benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose

Cas:63593-03-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.

TIANFU CHEM 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE

Cas:63593-03-3

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE

Cas:63593-03-3

Min.Order:1 Gram

FOB Price: $1.0 / 99.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Factory direct supply CAS 63593-03-3 with best quality

Cas:63593-03-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE CAS:63593-03-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemica

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE CAS:63593-03-3

Cas:63593-03-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

a-D-erythro-Pentofuranose,4-C-(hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

Cas:63593-03-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

a-D-erythro-Pentofuranose,4-C-(hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

3-O-Benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose

Cas:63593-03-3

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

A-D-ERYTHRO-PENTOFURANOSE,4-C-(HYDROXYMETHYL)-1,2-O-(1-METHYLETHYLIDENE)-3-O-(PHENYLMETHYL)-

Cas:63593-03-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

NewCan Biotech Limited

NewCan Biotech Limited was established in 2021 and is primarily engaged in the research, development, production, and sales of sugars, nucleosides, nucleotides, phosphorylated monomers, as well as next-generation antiviral and antitumor drug intermed

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

a-D-erythro-Pentofuranose,4-C-(hydroxymethyl)-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shaanxi Cuicheng Biomedical Technology Co., Ltd.

Why Choose Us: 1. Factory direct sales, so we can provide the competitive price and high quality product base on 8 years of production and R&D experience. 2. It is available in stock for quick shipment.Products could be packaged according to cu

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose

Cas:63593-03-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

YUNBIO TECH CO.,LTD

Our Strength: -Flexible: We work in small teams with rapid communication channels. Respond quickly and efficiently to customer and market needs. -Innovative: We are focusing on the development of new products and keep close relationships with

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE

Cas:63593-03-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE

Cas:63593-03-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Shanghai Minstar Chemical Co., Ltd

-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE Basic information Product Name: 3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE Synonyms: ((3aR,6S,6aR);-2,2-dimethyltetrahydrofuro[2,3

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-ALPHA-D-ERYTHROPENTOFURANOSE

Cas:63593-03-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-α-D-ERYTHROPENTOFURANOSE China supplier

Cas:63593-03-3

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-α-D-ERYTHROPENTOFURANOSE China supplier

Cas:63593-03-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-α-D-ERYTHROPENTOFURANOSE China supplier

Cas:63593-03-3

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

3-O-Benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-α-D-ERYTHROPENTOFURANOSE China supplier

Cas:63593-03-3

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

Hebei Mojin Biotechnology Co.,Ltd

1, High quality with competitive price:2, Fast and safe delivery3.Excellent pre-sales and after-sales service4. Well-trained and professional technologist and sales with rich experience in the field for 5-10 yearsAppearance:see detailed specification

Win-Win chemical Co.Ltd

Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai

3-O-BENZYL-4-(HYDROXYMETHYL-1,2-O-ISOPROPYLIDENE)-α-D-ERYTHROPENTOFURANOSE cas no. 63593-03-3 97%

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Kono Chem Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou

a-D-erythro-Pentofuranose,4-C-(hydroxymethyl)-1,2-O-(1-methy...

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Other

inquiry

GIHI CHEMICALS CO.,LIMITED

high purity,in stock Package:25kg/drum,or as per customers'demand Application:API,Pharmaceutical intermediates Transportation:air,sea,courier

3-O-Benzyl-4-(hydroxymethyl-1,2-O-isopropylidene-alpha-D-erythropentofuranose

Cas:63593-03-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

formaldehyd
50-00-0

formaldehyd

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
63593-02-2

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane Cannizzaro reaction;94%
With sodium hydroxide In 1,4-dioxane at 28 - 30℃; for 16.83h;75%
With sodium hydroxide In tetrahydrofuran; water at 20℃;47%
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;47%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃;52.5 g
1,2 5,6-O-di(isopropylidene)-α-D-allofuranose
620630-82-2

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose
57099-04-4

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaIO4 / methanol
2: 94 percent / aq. NaOH / dioxane
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate / water / 1 h / 0 °C
2: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
2: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose
22331-21-1

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / ethanol
2: aq. NaIO4 / methanol
3: 94 percent / aq. NaOH / dioxane
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water / 72 h / 20 °C
2: sodium periodate / water / 1 h / 0 °C
3: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water / 20 - 25 °C / Large scale
2: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
3: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
formaldehyd
50-00-0

formaldehyd

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 144h;77 g
Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere
1.2: 4.5 h / 0 °C
2.1: acetic acid / water / 72 h / 20 °C
3.1: sodium periodate / water / 1 h / 0 °C
4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale
2: acetic acid / water / 20 - 25 °C / Large scale
3: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
4: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere
1.2: 4.5 h / 0 °C
2.1: acetic acid / water / 72 h / 20 °C
3.1: sodium periodate / water / 1 h / 0 °C
4.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: acetic acid; water / 20 °C
3.1: sodium periodate / water; methanol / 1 h / 20 °C
4.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: acetic acid / water / 20 °C
3.1: sodium periodate / water; methanol / 1 h / 20 °C
4.1: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: acetic acid / water / 20 °C
3.1: sodium periodate / methanol; water / 1 h / 20 °C
4.1: sodium hydroxide / tetrahydrofuran; water / 20 °C
View Scheme
3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
1013943-40-2

3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; water / 20 °C
2: sodium periodate / water; methanol / 1 h / 20 °C
3: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water / 20 °C
2: sodium periodate / water; methanol / 1 h / 20 °C
3: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water / 20 °C
2: sodium periodate / methanol; water / 1 h / 20 °C
3: sodium hydroxide / tetrahydrofuran; water / 20 °C
View Scheme
C16H22O6

C16H22O6

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium periodate / water; methanol / 1 h / 20 °C
2: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate / water; methanol / 1 h / 20 °C
2: sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium periodate / methanol; water / 1 h / 20 °C
2: sodium hydroxide / tetrahydrofuran; water / 20 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: zinc(II) chloride; phosphoric acid / 15 - 30 °C / Large scale
2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C
3: sodium tetrahydroborate / water / 10 - 15 °C
4: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale
5: acetic acid / water / 20 - 25 °C / Large scale
6: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
7: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C
2: sodium tetrahydroborate / water / 10 - 15 °C
3: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale
4: acetic acid / water / 20 - 25 °C / Large scale
5: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
6: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose
2847-00-9

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium tetrahydroborate / water / 10 - 15 °C
2: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / toluene / 4 h / 30 - 90 °C / Large scale
3: acetic acid / water / 20 - 25 °C / Large scale
4: sodium periodate / water; tetrahydrofuran / 1.5 h / 10 °C / Large scale
5: sodium hydroxide / 1,4-dioxane / 16.83 h / 28 - 30 °C
View Scheme
vinyl acetate
108-05-4

vinyl acetate

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

5-O-acetyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

5-O-acetyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions
ConditionsYield
With candida antarctica lipase-B In di-isopropyl ether at 45℃; for 1.5h; Reagent/catalyst; Solvent; Green chemistry; Enzymatic reaction; regioselective reaction;100%
acetic anhydride
108-24-7

acetic anhydride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

4-C-(acetoxymethyl)-5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

4-C-(acetoxymethyl)-5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions
ConditionsYield
With dmap In dichloromethane; water at 20℃;99%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose
293751-01-6

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Conditions
ConditionsYield
With pyridine at 20℃; for 1h;98%
With pyridine at 0 - 20℃; for 1h;98%
With pyridine In dichloromethane98%
propionic acid anhydride
123-62-6

propionic acid anhydride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3-O-benzyl-1,2-O-isopropylidene-5-O-propanoyl-4-C-[(propanoyloxy)methyl]-α-D-ribofuranose

3-O-benzyl-1,2-O-isopropylidene-5-O-propanoyl-4-C-[(propanoyloxy)methyl]-α-D-ribofuranose

Conditions
ConditionsYield
With dmap In dichloromethane; water at 20℃;98%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3-O-benzyl-5-O-butanoyl-4-C-[(butanoyloxy)methyl]-1,2-O-isopropylidene-α-D-ribofuranose

3-O-benzyl-5-O-butanoyl-4-C-[(butanoyloxy)methyl]-1,2-O-isopropylidene-α-D-ribofuranose

Conditions
ConditionsYield
With dmap In dichloromethane; water at 20℃;98%
acetic anhydride
108-24-7

acetic anhydride

thymin
65-71-4

thymin

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

1-(2,5-di-O-acetyl-4-C-acetyloxymethyl-3-O-benzyl-β-D-erythro-pentofuranosyl)thymine
552856-36-7

1-(2,5-di-O-acetyl-4-C-acetyloxymethyl-3-O-benzyl-β-D-erythro-pentofuranosyl)thymine

Conditions
ConditionsYield
Stage #1: acetic anhydride; 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sulfuric acid In water; acetic acid at 0 - 20℃; for 2.41667h;
Stage #2: thymin With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 80℃; for 5h; Heating / reflux;
91%
benzyl bromide
100-39-0

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
153186-10-8

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Conditions
ConditionsYield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
73%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5 - 20℃; for 3h;69%
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In N,N-dimethyl-formamide; mineral oil at -5℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;
69%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol
212970-72-4

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Etherification; Silylation;67%
In dichloromethane at 20℃; for 11h;67%
benzyl chloride
100-44-7

benzyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

A

3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

B

{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol
153186-11-9

{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol

C

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
153186-10-8

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at -9℃; for 1h;A 10%
B 11%
C 66%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

A

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol
212970-72-4

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

B

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 1h; Heating;A 38%
B 62%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

A

C22H36O6Si
945628-28-4

C22H36O6Si

B

C22H36O6Si
314256-39-8

C22H36O6Si

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;A 22%
B 59%
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
153186-10-8

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Conditions
ConditionsYield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: With benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
51%
benzyl bromide
100-39-0

benzyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

A

3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

3,5,6-tri-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose

B

{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol
153186-11-9

{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol

C

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
153186-10-8

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Conditions
ConditionsYield
Stage #1: 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose With di(n-butyl)tin oxide In methanol for 1h; Substitution; Heating;
Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene for 15h; Etherification; Heating;
A 23%
B 21%
C 19%
acetic anhydride
108-24-7

acetic anhydride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Acetic acid (3S,4R)-4,5-diacetoxy-2-acetoxymethyl-3-benzyloxy-tetrahydro-furan-2-ylmethyl ester
552856-35-6

Acetic acid (3S,4R)-4,5-diacetoxy-2-acetoxymethyl-3-benzyloxy-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 20℃; for 2h;258 mg
With sulfuric acid In acetic acid at 0 - 20℃; for 2.41667h;
benzoyl chloride
98-88-4

benzoyl chloride

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose
552856-52-7

5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

1-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-thymine
945382-96-7

1-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-thymine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: acetic acid; triflic acid / 0.5 h
8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

C27H30N2O6

C27H30N2O6

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: acetic acid; triflic acid / 0.5 h
8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C
9.1: ammonia / methanol
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

1-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine
945382-98-9

1-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: acetic acid; triflic acid / 0.5 h
8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C
9.1: ammonia / methanol
10.1: 4.1 g / DMAP; pyridine
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

(1R,3R,4R,5R,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

(1R,3R,4R,5R,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: acetic acid; triflic acid / 0.5 h
8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C
9.1: ammonia / methanol
10.1: 4.1 g / DMAP; pyridine
11.1: Bu3SnH / toluene / 0.5 h / Heating
11.2: 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

(1R,3R,4R,5S,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

(1R,3R,4R,5S,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: acetic acid; triflic acid / 0.5 h
8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
8.2: 6 g / TMSOTf / acetonitrile / 0 - 20 °C
9.1: ammonia / methanol
10.1: 4.1 g / DMAP; pyridine
11.1: Bu3SnH / toluene / 0.5 h / Heating
11.2: 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose
945383-09-5

3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

C25H30O6

C25H30O6

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

3,5-di-O-benzyl-4-C-penten-yl-1,2-O-isopropylidene-α-D-ribofuranose
945383-12-0

3,5-di-O-benzyl-4-C-penten-yl-1,2-O-isopropylidene-α-D-ribofuranose

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

C27H32O7

C27H32O7

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
10.1: acetic acid; triflic acid / 0.5 h / ice bath
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

C30H34N2O7
945383-14-2

C30H34N2O7

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
10.1: acetic acid; triflic acid / 0.5 h / ice bath
11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
11.2: TMSOTf / acetonitrile / 0 - 20 °C
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine
945383-16-4

1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
10.1: acetic acid; triflic acid / 0.5 h / ice bath
11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
11.2: TMSOTf / acetonitrile / 0 - 20 °C
12.1: 2.8 g / ammonia / methanol
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine
945383-18-6

1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
10.1: acetic acid; triflic acid / 0.5 h / ice bath
11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
11.2: TMSOTf / acetonitrile / 0 - 20 °C
12.1: 2.8 g / ammonia / methanol
13.1: 60 percent / DMAP; pyridine
View Scheme
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
63593-03-3

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

(1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane
945383-20-0

(1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 66 percent / NaH / -5 - 20 °C
2.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
3.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
3.2: 17 g / tetrahydrofuran; hexane / -78 °C
4.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
4.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
5.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 1 h / 20 °C
6.2: 12 g / tetrahydrofuran; hexane / -78 °C
7.1: 9-borobicyclo(3.3.1)nonane / tetrahydrofuran
7.2: 90 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 20 °C
8.1: oxalyl chloride; DMSO; diisopropylethylamine / CH2Cl2 / -78 - 20 °C
9.1: BuLi / tetrahydrofuran; hexane / -78 °C
9.2: 3.5 g / tetrahydrofuran; hexane
10.1: acetic acid; triflic acid / 0.5 h / ice bath
11.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.75 h / Heating
11.2: TMSOTf / acetonitrile / 0 - 20 °C
12.1: 2.8 g / ammonia / methanol
13.1: 60 percent / DMAP; pyridine
14.1: Bu3SnH / toluene / 0.25 h / Heating
14.2: 76 percent / 2,2'-azobis(2-methyl-propionitrile; Bu3SnH / toluene / 2 h / Heating
View Scheme

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