Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester
• CAS No.: 225242-97-7
• Molecular Formula: C₁₈H₂₁N₃O₈S
• Molecular Weight: 439.446

Synonyms:Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester 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: 75.0%

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside (197663-12-0) → Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester (225242-97-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃;

DOI:10.1021/ja00061a053

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2) → Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester (225242-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / BF₃Et₂ / CH₂Cl₂

2: 75 percent / m-CPBA / CH₂Cl₂ / -78 °C

With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja00061a053

Reference yield:

thiophenol (108-98-5) → Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-benzenesulfinyl-tetrahydro-pyran-4-yl ester (225242-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / BF₃Et₂ / CH₂Cl₂

2: 75 percent / m-CPBA / CH₂Cl₂ / -78 °C

With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja00061a053

upstream raw materials:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

thiophenol

Downstream raw materials:

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threoninebenzyl ester

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