(2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester

Base Information

• Chemical Name: (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester
• CAS No.: 683210-54-0
• Molecular Formula: C₂₀H₂₉NO₉S
• Molecular Weight: 459.518

Synonyms:(2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester

Chemical Property of (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester

Chemical Property:

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Technology Process of (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester

There total 2 articles about (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic 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:

(2R,4'S,4R,5'R)-azide-(2',2',2,2-tetramethyl-[4',4]bis[[1,3]dioxolanyl]-5'-yl)-acetic acid methyl ester → (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester (683210-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 4 h / 40 °C / 3040 Torr

2: 4-DMAP / dimethylformamide / 20 °C

With dmap; hydrogen; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm0304313

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate (170997-51-0) → (2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester (683210-54-0)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0304313

Reference yield: 74.0%

(2R,4'S,4R,5R)-(4-methoxybenzenesulfonylamino)-[2',2',2,2-tetramethyl-[4',4]bi([1,3]dioxolanyl)-5'-yl]acetic acid methyl ester (683210-54-0) → (1R,2R,4'R,5'S)-[5'-(1,2-dihydroxyethyl)-2,2'-dimethyl[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)acetic acid methyl ester (683210-58-4)

Guidance literature:

With cerium(III) chloride; oxalic acid; In acetonitrile; at 20 ℃; for 1.16667h;

DOI:10.1021/jm0304313

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate

Downstream raw materials:

(1R,2R,4'R,5'S)-[5'-(1,2-dihydroxyethyl)-2,2'-dimethyl[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)acetic acid methyl ester

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