Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

Base Information

• Chemical Name: Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester
• CAS No.: 178812-57-2
• Molecular Formula: C₁₇H₂₂O₇
• Molecular Weight: 338.357

Synonyms:Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

Chemical Property of Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

Chemical Property:

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Technology Process of Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

There total 2 articles about Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-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: 88.0%

benzoyl chloride (98-88-4) + (3aR,4R,5S,8R,8aR)-5-Methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepine-4,8-diol (178812-55-0) → Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester (178812-57-2) + C24H26O8

Guidance literature:

With pyridine; for 0.5h;

DOI:10.1016/0008-6215(96)00024-9

Reference yield:

methyl 2-O-benzoyl-3,4-O-isopropylidene-α-D-xylo-hexoseptanosid-5-ulose (178812-59-4) → Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester (178812-57-2) + Benzoic acid (3aS,4R,5S,8S,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester (178812-62-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 0.0833333h;

DOI:10.1016/0008-6215(96)00024-9

Reference yield: 97.0%

p-toluenesulfonyl chloride (98-59-9) + Benzoic acid (3aS,4R,5S,8R,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester (178812-57-2) → Benzoic acid (3aS,4R,5S,8R,8aS)-5-methoxy-2,2-dimethyl-8-(toluene-4-sulfonyloxy)-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester (178812-58-3)

Guidance literature:

With pyridine; for 24h;

DOI:10.1016/0008-6215(96)00024-9

upstream raw materials:

benzoyl chloride

(3aR,4R,5S,8R,8aR)-5-Methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepine-4,8-diol

methyl 2-O-benzoyl-3,4-O-isopropylidene-α-D-xylo-hexoseptanosid-5-ulose

Downstream raw materials:

Benzoic acid (3aS,4R,5S,8R,8aS)-5-methoxy-2,2-dimethyl-8-(toluene-4-sulfonyloxy)-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

methyl 2-O-benzoyl-3,4-O-isopropylidene-α-D-xylo-hexoseptanosid-5-ulose

Benzoic acid (3aS,4R,5S,8S,8aR)-8-hydroxy-5-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-d]oxepin-4-yl ester

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