Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 849938-20-1
• Molecular Formula: C23H26O6S
• Molecular Weight: 430.522
• Mol file: 849938-20-1.mol

Synonyms:Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside;Phenyl 6-Deoxy-2-O-(phenylMethyl)-1-thio-α-L-Mannopyranoside Diacetate

Chemical Property of Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

• Melting Point: 95-97?C
• PSA: 96.36000
• LogP: 3.97230
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Phenyl3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside (cas# 849938-20-1) is a compound useful in organic synthesis.

Technology Process of Phenyl 3,4-Di-O-acetyl-α-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 1 articles about Phenyl 3,4-Di-O-acetyl-α-O-benzyl-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: 100.0%

phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-16-5) + acetic anhydride (108-24-7) → phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-20-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ol0500463

Reference yield: 84.0%

phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-20-1) → 3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide (849938-23-4)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol0500463

Reference yield:

phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside (849938-20-1) → Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside) (77307-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Br₂ / CH₂Cl₂ / 1 h / 0 °C

2: 60 percent / Ag₂O / CH₂Cl₂ / 4 h / 20 °C

3: 94 percent / H₂ / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h

With hydrogen; bromine; silver(l) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol0500463

upstream raw materials:

phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside

acetic anhydride

Downstream raw materials:

3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide

5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

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