S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside
• CAS No.: 134756-58-4
• Molecular Formula: C₁₉H₁₈O₃S
• Molecular Weight: 326.416
• Mol file: 134756-58-4.mol

Synonyms:S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Chemical Property of S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

There total 6 articles about S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 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:

benzaldehyde dimethyl acetal (1125-88-8) + thiophenyl 2,3-dideoxy-α-D-glucopyranoside (111425-52-6) → S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside (134756-58-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; Yield given;

DOI:10.1021/ja00015a051

Reference yield:

phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside (111425-49-1,125848-19-3,137740-45-5,111425-48-0,286410-13-7) → S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside (134756-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 1 h

2: p-toluenesulfonic acid / dimethylformamide / 9 h / 20 - 30 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

Reference yield:

3,4,6-O-tri-O-acetyl-D-glucal (69534-73-2) → C19H18O3S (134756-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / -78 °C

2: methanol; sodium methylate / 20 °C

3: toluene-4-sulfonic acid / 20 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In dichloromethane; 1: Ferrier rearrangement;

DOI:10.1021/jo102382r

upstream raw materials:

benzaldehyde dimethyl acetal

thiophenyl 2,3-dideoxy-α-D-glucopyranoside

phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

3,4,6-O-tri-O-acetyl-D-glucal

Downstream raw materials:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose

1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose