phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside
• CAS No.: 153693-37-9
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 153693-37-9.mol

Synonyms:phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

There total 6 articles about phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 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: 89.0%

acetic anhydride (108-24-7) + phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (153693-37-9)

Guidance literature:

With pyridine; at 20 ℃; for 24h; Time;

DOI:10.1016/j.carres.2021.108497

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (153693-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂, 85percent H₃PO₄ / 24 h / 25 °C

2: pyridine / 10 h / 25 °C

With pyridine; phosphoric acid; zinc(II) chloride;

DOI:10.1021/ja00084a018

Reference yield:

C15H20O5S + acetic anhydride (108-24-7) → phenyl 4,6-di-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-mannopyranoside + phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (153693-37-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/anie.201408209

upstream raw materials:

acetic anhydride

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

Downstream raw materials:

phenyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside

phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside

phenyl 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-thio-α-L-mannopyranoside