Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 143332-41-6
• Molecular Formula: C₂₂H₂₄O₇
• Molecular Weight: 400.428

Synonyms:Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-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:

benzoyl chloride (98-88-4) → Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester (143332-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / pyridine

With pyridine;

Reference yield:

Trimethyl orthoacetate (1445-45-0) + benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (105285-86-7) → Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester (143332-41-6)

Guidance literature:

Yield given. Multistep reaction;

Reference yield: 72.0%

2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-D-glucopyranosyl trichloroacetimidate (143394-76-7) + Benzoic acid (2S,3R,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester (143332-41-6) → (2S,4aR,6S,7R,8S,8aR)-6-((2R,3R,4R,5S,6S)-3-Acetoxy-5-benzoyloxy-2-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-7,8-bis-benzoyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (143332-44-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1h;

upstream raw materials:

Trimethyl orthoacetate

benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

benzoyl chloride

Downstream raw materials:

(2S,4aR,6S,7R,8S,8aR)-6-((2R,3R,4R,5S,6S)-3-Acetoxy-5-benzoyloxy-2-benzyloxy-6-methyl-tetrahydro-pyran-4-yloxy)-7,8-bis-benzoyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

C₇₂H₇₉NO₂₂

(2S,4aR,6S,7R,8S,8aR)-6-[(2S,3R,4R,5S,6S)-3-Acetoxy-5-benzoyloxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-7,8-bis-benzoyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

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