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

Base Information

Chemical Name:methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-hydroxypropyl)-D-penicillamine
CAS No.:253195-00-5
Molecular Formula:C₁₈H₂₉NO₈S₂
Molecular Weight:451.562
Hs Code.:

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

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Chemical Property of methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-hydroxypropyl)-D-penicillamine

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Technology Process of methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-hydroxypropyl)-D-penicillamine

There total 8 articles about methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-hydroxypropyl)-D-penicillamine 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: 78.0%

: 253194-99-9
methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2(S)-methoxymethoxy-3-tert-butyldimethylsiloxypropyl)-D-penicillamine

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/jm990330y

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With hydrogenchloride; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; 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;
DOI:10.1021/jm990330y

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With hydrogenchloride; dmap; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; 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;
DOI:10.1021/jm990330y