phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 868258-89-3
• Molecular Formula: C₂₉H₃₃N₃O₅S
• Molecular Weight: 535.664

Synonyms:phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 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: 65.0%

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-1-thio-β-D-glucopyranoside (868258-83-7) → phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (868258-89-3)

Guidance literature:

With cerium(III) chloride; In acetonitrile; for 24h; Heating;

DOI:10.1021/jm050368c

Reference yield:

phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (125085-03-2) → phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (868258-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NaH / dimethylformamide; tetrahydrofuran / 24 h

2: 65 percent / aq. Na₃N; CeCl₃ / acetonitrile / 24 h / Heating

With cerium(III) chloride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050368c

Reference yield: 47.0%

phenyl 4-O-((R)-3-azido-2-hydroxypropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (868258-89-3) + (R)-glycidyl tosylate (113826-06-5,6746-81-2) → phenyl 4-O-((R)-3-azido-2-((R)-glycidyl)propyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside (868258-90-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jm050368c

upstream raw materials:

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((R)-glycidyl)-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 4-O-((R)-3-azido-2-((R)-glycidyl)propyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

phenyl 4-O-((R)-2-acetoxyl-3-azidopropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-((S)-2,3-diazidopropyl)-1-thio-β-D-glucopyranoside

phenyl 4-O-((R)-2-((R)acetoxyl-3-azidopropyl)-3-azidopropyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside

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