(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester
CAS No.:321887-10-9
Molecular Formula:C₂₁H₂₅NO₁₀
Molecular Weight:451.43
Hs Code.:

Synonyms:(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

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Technology Process of (2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

There total 3 articles about (2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl 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: 100.0%

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

: 62-23-7
4-nitro-benzoic acid

: 321887-10-9
(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)01507-0

Reference yield:

: 138-59-0
shikimic acid

: 321887-10-9
(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / SOCl₂ / 10 °C

2: 90 percent / (+/-)-CSA / methanol / 48 h / 90 °C

3: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 5 h / 20 °C

With thionyl chloride; 10-camphorsufonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 3: Mitsunobu reaction;
DOI:10.1248/cpb.54.1459

Reference yield:

: 40983-58-2
methyl shikimate

: 321887-10-9
(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / (+/-)-CSA / methanol / 48 h / 90 °C

2: diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 5 h / 20 °C

With 10-camphorsufonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 2: Mitsunobu reaction;
DOI:10.1248/cpb.54.1459