(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

Base Information

Chemical Name:(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide
CAS No.:1260181-67-6
Molecular Formula:C₂₂H₂₃N₃O₇S
Molecular Weight:473.507
Hs Code.:

Synonyms:(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

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Chemical Property of (R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

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Technology Process of (R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

There total 7 articles about (R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide 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: 70.0%

: 1260181-59-6
phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-α-D-galactopyranoside

: 1260181-67-6
(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

: 1260181-69-8
(S)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -76 ℃;
DOI:10.1139/V10-091

Reference yield:

: 1260181-53-0
phenyl 2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-α-D-galactopyranoside

: 1260181-67-6
(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

: 1260181-69-8
(S)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 16 h / 20 °C

2: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / -76 °C

With pyridine; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1139/V10-091

Reference yield:

: phenyl 3,4,6-tetra-O-acetyl-2-azido-2-deoxy-1-thio-O-acetyl-D-galactopyranoside

: 1260181-67-6
(R)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

: 1260181-69-8
(S)-phenyl 3-O-acetyl-2-azido-2-deoxy-4,6-O-(p-methoxybenzylidene)-1-thio-a-D-galactopyranoside S-oxide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 1 h

1.2: Amberlite IR-120(H⁺)

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; benzene / 45 h / Reflux

3.1: pyridine / 16 h / 20 °C

4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / -76 °C

With pyridine; sodium methylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1139/V10-091