phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• CAS No.: 124476-96-6
• Molecular Formula: C₂₉H₃₂O₅S
• Molecular Weight: 492.636
• Mol file: 124476-96-6.mol

Synonyms:phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

There total 10 articles about phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-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: 95.0%

benzyl bromide (100-39-0) + phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (120095-47-8) → phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-96-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0008-6215(89)84061-3

Reference yield:

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) → phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.99 g / NaOMe / methanol / 2 h / pH 9

2: 50 percent / TsOH*H₂O / CH₂Cl₂ / 3 h

3: 86 percent / NaH / dimethylformamide / 0 - 20 °C

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00159-3

Reference yield:

D-galactose pentaacetate (25878-60-8) → phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-96-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

2: 5.99 g / NaOMe / methanol / 2 h / pH 9

3: 50 percent / TsOH*H₂O / CH₂Cl₂ / 3 h

4: 86 percent / NaH / dimethylformamide / 0 - 20 °C

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00159-3

upstream raw materials:

benzyl bromide

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

D-galactose pentaacetate

Downstream raw materials:

phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside