thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside

Base Information

• Chemical Name: thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside
• CAS No.: 785806-29-3
• Molecular Formula: C₄₀H₄₀O₅S
• Molecular Weight: 632.821
• Mol file: 785806-29-3.mol

Synonyms:thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside

Chemical Property of thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside

There total 7 articles about thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-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: 85.0%

phenyl 1-thio-D-galactopyranoside + benzyl bromide (100-39-0) → thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside (785806-29-3)

Guidance literature:

phenyl 1-thio-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1002/chem.201705511

Reference yield: 80.0%

1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9) + bis-(phenylthio)-dibutylstannane (14365-16-3) → thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside (785806-29-3)

Guidance literature:

With di-n-butylbis(trifluoromethanesulfonyloxy)stannane; In 1,2-dichloro-ethane; at 50 ℃; for 2h;

DOI:10.1016/0040-4039(92)88060-I

Reference yield:

D-galactose pentaacetate (25878-60-8) → thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside (785806-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 - 20 °C

2: sodium methylate; methanol

3: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

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

DOI:10.1039/c3ra46796a

upstream raw materials:

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

bis-(phenylthio)-dibutylstannane

benzyl bromide

thiophenol

Downstream raw materials:

methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside

methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran

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