methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Base Information

Chemical Name:methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
CAS No.:245054-37-9
Molecular Formula:C₂₁H₂₆O₈
Molecular Weight:406.433
Hs Code.:

Synonyms:methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

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Technology Process of methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

There total 9 articles about methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 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: 98.0%

: 98-88-4
benzoyl chloride

: 245054-31-3
(2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

: 245054-37-9
methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: With dmap; In pyridine; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00431-7

Reference yield: 90.0%

: 65-85-0,8013-63-6
benzoic acid

: 245054-32-4
methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

: 245054-37-9
methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/j.tetlet.2004.06.092

Reference yield:

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 245054-37-9
methyl (3S,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 84 percent / Ph₂S[OC(CF₃)2Ph]2 / CH₂Cl₂ / 24 h / 20 °C

3: 91 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

4: 90 percent / Ph₃P; diisopropylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C

With Martins sulfurane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 4: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2004.06.092