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
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inquiryAs 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
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inquiry3-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
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inquiryHello, 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
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inquiryHenan 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
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inquiryA 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
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inquiryCompany 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
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inquiryNewCan 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
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inquiryJ&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
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inquiryWhy 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
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inquiryZibo 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
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inquiryOur 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
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inquiryProduct 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,
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inquiryGMP 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,
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inquiry-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
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inquiryfactory?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
Cas:63593-03-3
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inquiryShandong 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
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inquiry1.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
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inquiryHigh 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
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inquiryWe 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
Cas:63593-03-3
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inquiry1, 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
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inquiryStock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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inquiryhigh 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
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inquiryhigh purity,in stock Package:25kg/drum,or as per customers'demand Application:API,Pharmaceutical intermediates Transportation:air,sea,courier
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inquiryformaldehyd
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
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 144h; | 77 g |
Diacetone D-glucose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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 |
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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 |
D-glucofuranose
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
With dmap In dichloromethane; water at 20℃; | 99% |
methanesulfonyl chloride
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
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 98% |
With pyridine at 0 - 20℃; for 1h; | 98% |
With pyridine In dichloromethane | 98% |
propionic acid anhydride
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
With dmap In dichloromethane; water at 20℃; | 98% |
butanoic acid anhydride
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
Conditions | Yield |
---|---|
With dmap In dichloromethane; water at 20℃; | 98% |
acetic anhydride
thymin
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 14h; Etherification; Silylation; | 67% |
In dichloromethane at 20℃; for 11h; | 67% |
benzyl chloride
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-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
C
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at -9℃; for 1h; | A 10% B 11% C 66% |
tert-butylchlorodiphenylsilane
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
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane for 1h; Heating; | A 38% B 62% |
tert-butyldimethylsilyl chloride
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose
A
C22H36O6Si
B
C22H36O6Si
Conditions | Yield |
---|---|
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
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
Conditions | Yield |
---|---|
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
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-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
C
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; |
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
3,5-di-O-benzyl-4-C-hydroxypropyl-1,2-O-isopropylidene-α-D-ribofuranose
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
3,5-di-O-benzyl-4-C-penten-yl-1,2-O-isopropylidene-α-D-ribofuranose
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
C30H34N2O7
Conditions | Yield |
---|---|
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
1-[3,5-di-O-benzyl-4-C-penten-yl-2-hydroxy-β-D-ribofuranosyl]-thymine
Conditions | Yield |
---|---|
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
1-[3,5-di-O-benzyl-4-C-penten-yl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-thymine
Conditions | Yield |
---|---|
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
(1R,2R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane
Conditions | Yield |
---|---|
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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