Product Name

Synthetic route

benzyl bromide
100-39-0

benzyl bromide

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol
117641-39-1

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Stage #1: (2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 12h;		86%
With tetra-(n-butyl)ammonium iodide; sodium hydride 1.) THF, 2 h; 1.) THF, 2.5 h; Yield given. Multistep reaction;
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide Yield given;
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at -50℃; for 18h;
With sodium hydride In tetrahydrofuran; water at 20℃; Large scale;4.4 kg
Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: NaH / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 2 h / -40 °C
2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C
2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C
3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C
4.1: NaH / tetrahydrofuran / 1 h / 20 °C
4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / -78 - -65 °C
2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C
3: VO(acac)2, t-BuOOH / CH2Cl2
4: NaH, Bu4NI / dimethylformamide
View Scheme
Multi-step reaction with 4 steps
1: 1.) Na / 1.) THF, -5 deg C, 1.5 h; 2.) THF, -45 deg C, 1 h
2: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h
3: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C
4: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h
View Scheme
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C
1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C
2.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C
3.1: NaH / tetrahydrofuran / 1 h / 20 °C
3.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C
2: VO(acac)2, t-BuOOH / CH2Cl2
3: NaH, Bu4NI / dimethylformamide
View Scheme
Multi-step reaction with 3 steps
1: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h
2: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C
3: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h
View Scheme
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(AsCF3)4.5

(AsCF3)4.5

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: NaH / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 2 h / -40 °C
2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C
2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C
3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C
4.1: NaH / tetrahydrofuran / 1 h / 20 °C
4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C
View Scheme
(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene
110567-21-0

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C
2.1: NaH / tetrahydrofuran / 1 h / 20 °C
2.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: VO(acac)2, t-BuOOH / CH2Cl2
2: NaH, Bu4NI / dimethylformamide
View Scheme
Multi-step reaction with 2 steps
1: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C
2: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h
View Scheme
Multi-step reaction with 2 steps
1.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / dichloromethane / 16 h / 20 °C / Large scale
1.2: 1 h / 20 °C / Large scale
2.1: sodium hydride / water; tetrahydrofuran / 20 °C / Large scale
View Scheme
sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / -78 - -65 °C
2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C
3: VO(acac)2, t-BuOOH / CH2Cl2
4: NaH, Bu4NI / dimethylformamide
View Scheme
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) Na / 1.) THF, -5 deg C, 1.5 h; 2.) THF, -45 deg C, 1 h
2: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h
3: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C
4: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,2R,3S,5R)-2-Hydroxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-ol
117641-42-6

(1S,2R,3S,5R)-2-Hydroxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-ol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal100%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol
110567-23-2

(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

Conditions
ConditionsYield
With sodium azide; ammonium chloride In ethanol at 85℃; for 22h;99%
With sodium azide; ammonium chloride In ethanol at 85℃; for 22h;
C17H19N5O3
1351691-90-1

C17H19N5O3

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

C37H41N5O6

C37H41N5O6

Conditions
ConditionsYield
Stage #1: C17H19N5O3 With lithium hydride In N,N-dimethyl-formamide at 60℃; for 0.25h;
Stage #2: (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane In N,N-dimethyl-formamide at 125℃; for 2.5h;		83%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

potassium cyanide
151-50-8

potassium cyanide

(1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane
160860-62-8

(1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane

Conditions
ConditionsYield
With lithium perchlorate In acetonitrile at 70℃; for 96h;77.5%
With lithium perchlorate In acetonitrile at 70℃; for 24h;75%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

2,4-dihydroxy-5-methylpyrimidine
65-71-4

2,4-dihydroxy-5-methylpyrimidine

1-(3',5'-di-O-benzyl-2'-deoxy-6'-hydroxy-6'-carba-β-D-ribofuranosyl)thymine
114071-49-7

1-(3',5'-di-O-benzyl-2'-deoxy-6'-hydroxy-6'-carba-β-D-ribofuranosyl)thymine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 140℃;70%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

thymin
65-71-4

thymin

1-(3',5'-di-O-benzyl-2'-deoxy-6'-hydroxy-6'-carba-β-D-ribofuranosyl)thymine
114071-49-7

1-(3',5'-di-O-benzyl-2'-deoxy-6'-hydroxy-6'-carba-β-D-ribofuranosyl)thymine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 140℃;70%
With lithium hydride In N,N-dimethyl-formamide at 140℃;64%
Stage #1: thymin With triethylaluminum In tetrahydrofuran; hexane at 20℃; for 1h;
Stage #2: (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane In tetrahydrofuran; hexane at 20℃; for 48h; ultrasound;		46%
In N-methyl-acetamide; methanol; dichloromethane; acetic acid; toluene; mineral oil
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

adenine
66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9

adenine

[1S-(1α,2β,3α,5β)]-5-(6-amino-9H-purin-9-yl)-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]cyclopentanol
142217-96-7

[1S-(1α,2β,3α,5β)]-5-(6-amino-9H-purin-9-yl)-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]cyclopentanol

Conditions
ConditionsYield
With lithium hydride In N,N-dimethyl-formamide at 120℃;70%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

uracil
66-22-8

uracil

[1S-(1α,2β,3α,4β)]-1-[2-Hydroxy-4-(phenyl-methoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]-2,4(1H,3H)-pyrimidinedione
114071-48-6

[1S-(1α,2β,3α,4β)]-1-[2-Hydroxy-4-(phenyl-methoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]-2,4(1H,3H)-pyrimidinedione

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 130℃;65%
With sodium hydride In N,N-dimethyl-formamide at 140℃;63%
With acetic acid In N-methyl-acetamide; methanol; dichloromethane; mineral oil
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

2-Amino-6-benzyloxypurine
19916-73-5

2-Amino-6-benzyloxypurine

[1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol
142217-77-4

[1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol

Conditions
ConditionsYield
With lithium hydride In N,N-dimethyl-formamide at 125℃; for 2h;60%
Stage #1: 2-Amino-6-benzyloxypurine With lithium hydride In N,N-dimethyl-formamide at 20 - 60℃; for 0.416667h;
Stage #2: (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane In N,N-dimethyl-formamide at 60 - 125℃; for 2.25h;		51.18%
With acetic acid In N-methyl-acetamide; methanol; ethanol; dichloromethane; chloroform
With tetrabutylammomium bromide; potassium hydroxide In toluene at 80℃; for 6h; Temperature; Reagent/catalyst;6 g
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

2-[(triphenylmethyl)amino]-6-benzyloxy-9H-purine

2-[(triphenylmethyl)amino]-6-benzyloxy-9H-purine

(1S,2S,3S,5S)-3-(benzyloxy)-5-[6-(benzyloxy)-2-[(triphenylmethyl)amino]-9H-purin-9-yl]-2-[(benzyloxy)methyl]cyclopentan-1-ol

(1S,2S,3S,5S)-3-(benzyloxy)-5-[6-(benzyloxy)-2-[(triphenylmethyl)amino]-9H-purin-9-yl]-2-[(benzyloxy)methyl]cyclopentan-1-ol

Conditions
ConditionsYield
Stage #1: 2-[(triphenylmethyl)amino]-6-benzyloxy-9H-purine With lithium hydride In N,N-dimethyl-formamide at 58 - 62℃; for 0.5h;
Stage #2: (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane In N,N-dimethyl-formamide at 60 - 120℃; for 0.5h;		58.5%
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

2-amino-6-methoxyethoxypurine

2-amino-6-methoxyethoxypurine

(1S,2S,3S,5S)-5-[2-Amino-6-(2-methoxy-ethoxy)-purin-9-yl]-3-benzyloxy-2-benzyloxymethyl-cyclopentanol
114071-50-0

(1S,2S,3S,5S)-5-[2-Amino-6-(2-methoxy-ethoxy)-purin-9-yl]-3-benzyloxy-2-benzyloxymethyl-cyclopentanol

Conditions
ConditionsYield
lithium hydride In N,N-dimethyl-formamide at 145℃;
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

A

(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol
110567-23-2

(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

B

(1R,2R,3R,4S)-2-Azido-4-benzyloxy-3-benzyloxymethyl-cyclopentanol

(1R,2R,3R,4S)-2-Azido-4-benzyloxy-3-benzyloxymethyl-cyclopentanol

Conditions
ConditionsYield
With sodium azide; ammonium chloride In ethanol; water for 22h; Heating;A 3.3 g
B 0.2 g
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

5'-O-[1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)thymidinyl]monophosphate

5'-O-[1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)thymidinyl]monophosphate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
3.1: 398 mg / AIBN; n-Bu3SnH / toluene / 3.5 h / 75 °C
4.1: 90 percent / BCl3 / CH2Cl2 / 5 h / -78 °C
5.1: i-Pr2NEt / acetonitrile; dimethylformamide / 2 h / -40 - 0 °C
6.1: 107 mg / t-BuOOH / acetonitrile; dimethylformamide / 2 h / -40 - 20 °C
7.1: 76 percent / Et3N; H2O / acetonitrile / 18 h / 20 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione
114884-15-0

1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
3.1: 398 mg / AIBN; n-Bu3SnH / toluene / 3.5 h / 75 °C
4.1: 90 percent / BCl3 / CH2Cl2 / 5 h / -78 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)thymine
648414-58-8

1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)thymine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
3.1: 398 mg / AIBN; n-Bu3SnH / toluene / 3.5 h / 75 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

1-{(3S,1R,4R)-3-hydroxy-4-(8-methyl-2-oxo(4H-benzo[d]1,3,2-dioxaphosphan-2-yloxy)methylcyclopentyl)}-5-methyl-1,3-dihydropyrimidine-2,4(1H,3H)-dione

1-{(3S,1R,4R)-3-hydroxy-4-(8-methyl-2-oxo(4H-benzo[d]1,3,2-dioxaphosphan-2-yloxy)methylcyclopentyl)}-5-methyl-1,3-dihydropyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
3.1: 398 mg / AIBN; n-Bu3SnH / toluene / 3.5 h / 75 °C
4.1: 90 percent / BCl3 / CH2Cl2 / 5 h / -78 °C
5.1: i-Pr2NEt / acetonitrile; dimethylformamide / 2 h / -40 - 0 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

3-methyl-cyclosaligenyl-5'-O-[1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)thymidinyl]-phosphate
648414-62-4

3-methyl-cyclosaligenyl-5'-O-[1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)thymidinyl]-phosphate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
3.1: 398 mg / AIBN; n-Bu3SnH / toluene / 3.5 h / 75 °C
4.1: 90 percent / BCl3 / CH2Cl2 / 5 h / -78 °C
5.1: i-Pr2NEt / acetonitrile; dimethylformamide / 2 h / -40 - 0 °C
6.1: 107 mg / t-BuOOH / acetonitrile; dimethylformamide / 2 h / -40 - 20 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

thiocarbonic acid O-[3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl] ester O-phenyl ester

thiocarbonic acid O-[3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl] ester O-phenyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Et3Al / hexane; tetrahydrofuran / 1 h / 20 °C
1.2: 46 percent / hexane; tetrahydrofuran / 48 h / 20 °C / ultrasound
2.1: DMAP / acetonitrile / 16 h / 20 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(S)-Methanocarba-Thymidine
156044-00-7

(S)-Methanocarba-Thymidine

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
4: benzophenone / benzene; acetonitrile / 2 h / Irradiation
5: 25percent aq. NaOH / methanol / 24 h / Heating
6: Et3N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h
7: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight
8: 99 percent / Bu4NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C
9: 85.5 percent / CH2Cl2 / 24 h / Ambient temperature
10: 2 M HCl / ethanol / 30 h / Heating
11: 87.72 percent / HCOOH / Pd / methanol / 2 h / 40 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-aminobicyclo<3.1.0>hexane
170453-02-8

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-aminobicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
4: benzophenone / benzene; acetonitrile / 2 h / Irradiation
5: 25percent aq. NaOH / methanol / 24 h / Heating
6: Et3N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h
7: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight
8: 99 percent / Bu4NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene
170452-98-9

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-cyanobicyclo<3.1.0>hexane
170453-00-6

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-cyanobicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
4: benzophenone / benzene; acetonitrile / 2 h / Irradiation
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid
190195-74-5

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
4: benzophenone / benzene; acetonitrile / 2 h / Irradiation
5: 25percent aq. NaOH / methanol / 24 h / Heating
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(3aR,4R,5S,6aR)-4-Benzyloxymethyl-5-benzyloxy-6a-cyano-3,3a,4,5,6,6a-hexahydrocyclopentapyrazole
170452-99-0

(3aR,4R,5S,6aR)-4-Benzyloxymethyl-5-benzyloxy-6a-cyano-3,3a,4,5,6,6a-hexahydrocyclopentapyrazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
View Scheme
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane
110567-22-1

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo<3.1.0>hexane
190195-79-0

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo<3.1.0>hexane

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 77.5 percent / LiClO4 / acetonitrile / 96 h / 70 °C
2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min
3: 96.5 percent / CHCl3; diethyl ether / 72 h / 0 °C
4: benzophenone / benzene; acetonitrile / 2 h / Irradiation
5: 25percent aq. NaOH / methanol / 24 h / Heating
6: Et3N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h
7: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight
8: 99 percent / Bu4NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C
9: 85.5 percent / CH2Cl2 / 24 h / Ambient temperature
10: 2 M HCl / ethanol / 30 h / Heating
View Scheme

(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Specification

The CAS registry number of (1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane is 110567-22-1. The molecular formula is C20H22O3 and the molecular weight is 310.39. In addition, the systematic name is (1S,2R,3S,5R)-3-(benzyloxy)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane. It belongs to the classes of Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals. What's more, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 3.58; (2)ACD/LogD (pH 5.5): 4; (3)ACD/LogD (pH 7.4): 4; (4)ACD/BCF (pH 5.5): 1200; (5)ACD/BCF (pH 7.4): 1200; (6)ACD/KOC (pH 5.5): 5569; (7)ACD/KOC (pH 7.4): 5569; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 7; (10)Polar Surface Area: 30.99 Å2; (11)Index of Refraction: 1.593; (12)Molar Refractivity: 89.559 cm3; (13)Molar Volume: 264.428 cm3; (14)Polarizability: 35.504 ×10-24cm3; (15)Surface Tension: 46.879 dyne/cm; (16)Density: 1.174 g/cm3; (17)Flash Point: 145.852 °C; (18)Enthalpy of Vaporization: 65.656 kJ/mol; (19)Boiling Point: 427.928 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O(Cc1ccccc1)[C@@H]2[C@H]([C@@H]3O[C@@H]3C2)COCc4ccccc4
(2)InChI: InChI=1/C20H22O3/c1-3-7-15(8-4-1)12-21-14-17-18(11-19-20(17)23-19)22-13-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18+,19-,20+/m1/s1
(3)InChIKey: YPDRJNPIGFCETD-WCIQWLHIBP

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