Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 203435-12-5
• Molecular Formula: C₂₅H₂₉NO₇
• Molecular Weight: 455.508

Synonyms:Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl 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: 91.0%

benzoyl chloride (98-88-4) + N-((2R,3R,4S,5S,6R)-4-Allyloxy-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide (203435-11-4) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (203435-12-5)

Guidance literature:

With pyridine; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/jo971784a

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (176300-16-6) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (203435-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, room temperature, 1 h

2: 91 percent / camphorsulfonic acid / methanol / 1 h / 60 °C

3: 91 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

With pyridine; camphor-10-sulfonic acid; sodium hydride; In methanol; dichloromethane;

DOI:10.1021/jo971784a

Reference yield:

N-((2R,4aR,6R,7R,8S,8aS)-8-Allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (203435-10-3) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetylamino-4-allyloxy-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (203435-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / camphorsulfonic acid / methanol / 1 h / 60 °C

2: 91 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

With pyridine; camphor-10-sulfonic acid; In methanol; dichloromethane;

DOI:10.1021/jo971784a

upstream raw materials:

benzoyl chloride

N-((2R,3R,4S,5S,6R)-4-Allyloxy-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

N-((2R,4aR,6R,7R,8S,8aS)-8-Allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

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