Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 108740-74-5
• Molecular Formula: C18H22O7S
• Molecular Weight: 382.434
• Mol file: 108740-74-5.mol

Synonyms:Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside;Phenyl 6-Deoxy-1-thio-α-L-Mannopyranoside Triacetate

Chemical Property of Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

• Melting Point: 106-109°C
• PSA: 113.43000
• LogP: 2.31860
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

99.3% ^*data from raw suppliers

Phenyl2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside (cas# 108740-74-5) is a compound useful in organic synthesis.

Technology Process of Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside

There total 21 articles about Phenyl 2,3,4-Tri-O-acetyl-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: 99.0%

thiophenol (108-98-5) + 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose (30021-94-4) → phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (108740-74-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.05h; sonication;

DOI:10.1021/jo060374w

Reference yield: 96.0%

acetic anhydride (108-24-7) + phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (108740-74-5)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 4.5h;

DOI:10.1002/ejoc.200500555

Reference yield: 93.0%

L-rhamnose (73-34-7) + acetic anhydride (108-24-7) + thiophenol (108-98-5) → phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (108740-74-5)

Guidance literature:

L-rhamnose; acetic anhydride; With magnesium triflate; at 20 ℃; for 0.05h; Inert atmosphere;

thiophenol; With boron trifluoride diethyl etherate; at 0 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.7b00561

upstream raw materials:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

phenylthiotrimethylsilane

L-rhamnose

acetic anhydride

Downstream raw materials:

4-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)benzaldehyde

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

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

(2S,3S,4S)-6-Benzenesulfonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

Refernces

• 1、 Fejedelem, Zachary,Carney, Nolan,Nagorny, Pavel. "Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B". . p. 10249 - 10262. Retrieved 2021/07/31.
• 2、 Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao. "Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions". . . Retrieved 2022/02/07.