Benzyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside

Base Information

• Chemical Name: Benzyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside
• CAS No.: 210358-01-3
• Molecular Formula: C41H42 O5 S
• Molecular Weight: 646.847
• DSSTox Substance ID: DTXSID70447903
• Nikkaji Number: J1.369.175D
• Wikidata: Q82266802
• Mol file: 210358-01-3.mol

Synonyms:210358-01-3;BENZYL 2,3,4,6-TETRA-O-BENZYL-1-THIO-BETA-D-GALACTOPYRANOSIDE;1,2,3,4,6-Penta-O-benzyl-b-D-thiogalactopyranoside;(2S,3R,4S,5S,6R)-2-benzylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane;(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(benzylthio)tetrahydro-2H-pyran;1,2,3,4,6-Penta-O-benzyl-beta-D-thiogalactopyranoside;DTXSID70447903;AKOS025294891;BS-22058;W-201851;Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-1-thio-beta-D-galactopyranoside;(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(benzylthio)tetrahydro-2H-pyran

Chemical Property of Benzyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside

Chemical Property:

• PSA: 71.45000
• LogP: 8.61770
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 646.27529561
• Heavy Atom Count: 47
• Complexity: 813

Purity/Quality:

98% ^*data from raw suppliers

1,2,3,4,6-Penta-O-benzyl-b-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)SCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)SCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Uses: 1,2,3,4,6-Penta-O-benzyl-β-D-thiogalactopyranoside (CAS# 210358-01-3) is a useful saccharide used in the preparation of carbohydrates and trisaccharides.

Technology Process of Benzyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside

There total 13 articles about Benzyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside 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: 84.0%

2-bromobenzyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside → benzyl 1-thio-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (210358-01-3)

Guidance literature:

With methanol; tert.-butyl lithium; In diethyl ether; hexane; at -78 ℃; for 0.516667h;

DOI:10.1016/j.carres.2014.05.010

Reference yield:

C43H41NO7 + benzyl alcohol (100-51-6,185532-71-2) → benzyl 1-thio-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (210358-01-3) + benzyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside (437757-82-9)

Guidance literature:

With gold(III) chloride; 3F₆Sb^(1-)*3Ag⁽¹⁺⁾; In dichloromethane; at 20 ℃; for 6h; Overall yield = 57 %; Inert atmosphere;

DOI:10.1039/c5ob00248f

Reference yield:

D-galactose pentaacetate (25878-60-8) → benzyl 1-thio-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (210358-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 20 h / 20 °C

2: MeONa / methanol

3: 3.65 g / NaH / dimethylformamide

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 2: Zemplen reaction;

DOI:10.1002/1099-0690(200204)2002:7<1305::AID-EJOC1305>3.0.CO;2-0

upstream raw materials:

D-galactose pentaacetate

phenylmethanethiol

acetobromogalactose

(2-bromophenyl)methanethiol

Downstream raw materials:

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

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