Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

Base Information

• Chemical Name: Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside
• CAS No.: 74801-29-9
• Molecular Formula: C40H40 O5 S
• Molecular Weight: 632.821
• Mol file: 74801-29-9.mol

Synonyms:Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside;Gal-beta-SPh[2346Bn];Phenyl 2,3,4,6-Tetra-O-benzyl-1-thio-beta-D-galactopyranoside

Chemical Property of Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 89 °C
• Refractive Index: 1.641
• Boiling Point: 738.515oC at 760 mmHg
• Flash Point: 400.44oC
• PSA: 71.45000
• Density: 1.224g/cm3
• LogP: 8.47660
• Storage Temp.: Freezer
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenyl 2,3,4,6-Tetra-O-benzyl-1-thio-β-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenyl 2,3,4,6-Tetra-O-benzyl-1-thio-β-D-galactopyranoside (cas# 74801-29-9) is a compound useful in organic synthesis.

Technology Process of Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside

There total 53 articles about Phenyl2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside 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: 98.0%

phenyl 1-thio-D-glucopyranoside (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) + benzyl bromide (100-39-0) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside (91602-61-8,38184-10-0,62774-37-2,74801-29-9,116501-52-1,116501-53-2,139974-84-8)

Guidance literature:

phenyl 1-thio-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; paraffin; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; paraffin; at 0 - 20 ℃;

DOI:10.3762/bjoc.8.46

Reference yield: 97.0%

thiophenol (108-98-5) + Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-59-2) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside (91602-61-8,38184-10-0,62774-37-2,74801-29-9,116501-52-1,116501-53-2,139974-84-8)

Guidance literature:

ytterbium(III) triflate; In acetonitrile; at 53 ℃; for 6h;

DOI:10.1016/S0040-4039(00)73563-5

Reference yield: 95.0%

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3) + benzyl bromide (100-39-0) → phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (74801-29-9)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2005.03.007

upstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

bis-(phenylthio)-dibutylstannane

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

2,3,4,6-tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

(2S,3R,4S,5S,6R)-2-((R)-Benzenesulfinyl)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

2,3,4,6-tetra-O-benzyl-α-D-galactopyranose

2,3,4,6-tetra-O-benzyl-D-galactopyranose

Refernces

• 1、 Kim, Sungjin,Nagorny, Pavel. "Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent". . p. 2294 - 2298. Retrieved 2022/04/07.
• 2、 Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen. "Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers". supporting information. p. 7680 - 7686. Retrieved 2019/05/22.