phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside
• CAS No.: 698372-46-2
• Molecular Formula: C₃₃H₃₃NO₆S
• Molecular Weight: 571.694
• Mol file: 698372-46-2.mol

Synonyms:phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside

There total 2 articles about phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-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: 93.0%

thiophenol (108-98-5) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside (698372-46-2)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 24h; optical yield given as %de; stereoselective reaction; Molecular sieve;

DOI:10.1021/jo900609s

Reference yield: 70.0%

thiophenol (108-98-5) + 3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside (698372-46-2) + phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-α-D-galactopyranoside

Guidance literature:

With caesium carbonate; 1,3-bis(mesityl)imidazolium chloride; In dichloromethane; at 20 ℃; for 24h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1055/s-0039-1690099

Reference yield: 70.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside (698372-46-2) → 2-(trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranoside

Guidance literature:

2-(Trimethylsilyl)ethanol; phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-galactopyranoside; With N-iodo-succinimide; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/ol049729t

upstream raw materials:

thiophenol

3,4,6-tri-O-benzyl-2-nitro-D-galactal

Downstream raw materials:

O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(benzoyl)-L-serine methyl ester

isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranoside

2-(trimethylsilyl)ethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-(1->6)-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranoside)