3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose

Base Information

• Chemical Name: 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose
• CAS No.: 1300590-29-7
• Molecular Formula: C₄₀H₄₈O₆Si
• Molecular Weight: 652.903
• Mol file: 1300590-29-7.mol

Synonyms:3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose

Chemical Property of 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose

There total 3 articles about 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol (287737-62-6) → 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose (1300590-29-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

Reference yield:

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole (287737-63-7) → 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose (1300590-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

With dmap; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane;

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → 3,5-di-O-benzyl-4-(2-t-butyldiphenylsilyloxyethyl)-1,2-O-isopropylidene-α-D-erythropentofuranose (1300590-29-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 4 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 12 h / 20 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; sulfur trioxide pyridine complex; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

tert-butylchlorodiphenylsilane

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

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

(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

3,5-di-O-benzyl-4-C-(2-t-butyldiphenylsilyloxyethyl)1,2-di-O-acetyl-α-D-erythropentofuranose

(2’R)-2’-amino-3’,5’-di-O-benzyl-4’-(2-carboxymethyl)thymidine

(2’R)-3’-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine

(2’R)-5’-O-(4,4’-dimethoxytrityl)-2’,4’-(N-methyl-2-oxoiminoethano)thymidine