methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

Base Information

Chemical Name:methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate
CAS No.:204129-80-6
Molecular Formula:C₁₈H₂₇NO₇S₂
Molecular Weight:433.547
Hs Code.:

Synonyms:methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

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Chemical Property of methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

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Technology Process of methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

There total 8 articles about methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-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: 86.0%

: 253195-00-5
methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-hydroxypropyl)-D-penicillamine

: 204129-80-6
methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/jm990330y

Reference yield:

: 52-67-5
3,3-dimethyl-D-cysteine

: 204129-80-6
methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 2 N aq. NaOH / ethanol / 20 °C

2: Et₃N / dioxane; H₂O / 18 h / 20 °C

3: methanol; diethyl ether

4: 1 N aq. HCl / tetrahydrofuran / 20 °C

5: 82 percent / Et₃N; (dimethylamino)pyridine / CH₂Cl₂ / 20 °C

6: 71 percent / NaI; i-Pr₂NEt / 1,2-dimethoxy-ethane / 4 h / Heating

7: 78 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

8: 86 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; 1: Alkylation / 2: sulfonylation / 3: Esterification / 4: Hydrolysis / 5: silylation / 6: Alkylation / 7: desilylation / 8: Cyclization;
DOI:10.1021/jm990330y

Reference yield:

: (S)-2-Amino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylsulfanyl)-3-methyl-butyric acid

: 204129-80-6
methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / dioxane; H₂O / 18 h / 20 °C

2: methanol; diethyl ether

3: 1 N aq. HCl / tetrahydrofuran / 20 °C

4: 82 percent / Et₃N; (dimethylamino)pyridine / CH₂Cl₂ / 20 °C

5: 71 percent / NaI; i-Pr₂NEt / 1,2-dimethoxy-ethane / 4 h / Heating

6: 78 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

7: 86 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; dmap; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; 1: sulfonylation / 2: Esterification / 3: Hydrolysis / 4: silylation / 5: Alkylation / 6: desilylation / 7: Cyclization;
DOI:10.1021/jm990330y