phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside
• CAS No.: 160140-48-7
• Molecular Formula: C₂₄H₃₄O₄SSi
• Molecular Weight: 446.683
• Mol file: 160140-48-7.mol

Synonyms:phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside

Chemical Property of phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside

There total 9 articles about phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (3R,4R,5R)-4-Benzyloxy-5-hydroxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-ol → phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside (160140-48-7) + phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-β-D-xylofuranoside (160140-49-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)76839-0

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside (160140-48-7)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 15 h / 25 °C

2: 50percent aq. acetic acid / 5 h / 100 °C

3: 94 percent / (n-Bu₃)P / tetrahydrofuran / 0.5 h / 25 °C

4: MeLi / diethyl ether / 0.25 h / 25 °C

5: imidazole / dimethylformamide / 0.5 h / 25 °C

With 1H-imidazole; tributylphosphine; methyllithium; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.67.3057

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl ester → phenyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-1-thio-α-D-xylofuranoside (160140-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / (n-Bu₃)P / tetrahydrofuran / 0.5 h / 25 °C

2: MeLi / diethyl ether / 0.25 h / 25 °C

3: imidazole / dimethylformamide / 0.5 h / 25 °C

With 1H-imidazole; tributylphosphine; methyllithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.67.3057

upstream raw materials:

tert-butyldimethylsilyl chloride

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

2,2-Dimethyl-propionic acid (3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

diphenyldisulfane

Downstream raw materials:

phenyl 2,3-di-O-benzyl-1-thio-α-D-xylofuranoside

(2R,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-(tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester

(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.0^3,7]tetradecane-6-carboxylic acid benzyl ester