(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester
• CAS No.: 477200-07-0
• Molecular Formula: C₂₄H₃₃NO₆SSi
• Molecular Weight: 491.681

Synonyms:(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester

Chemical Property of (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester

Chemical Property:

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Technology Process of (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester

There total 3 articles about (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-6-carboxylic acid ethyl 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: 85.0%

(2R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-sulfamoyloxy-pentanoic acid ethyl ester (477200-06-9) → (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ6-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester (477200-07-0)

Guidance literature:

With dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide; In dichloromethane;

DOI:10.1021/ja028139s

Reference yield:

ethyl (2R)-4-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-pentenoate (208242-93-7) → (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ6-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester (477200-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂; Rh(cod)2OTf; (R)-4,12-bis(diphenylphosphino)-[2,2]-paracyclophane / CH₂Cl₂ / 51716.2 Torr

2: ClSO₂NCO; HCO₂H

3: 85 percent / Rh₂(OAc)4; PhI(OAc)2; MgO / CH₂Cl₂

With dirhodium tetraacetate; formic acid; isocyanate de chlorosulfonyle; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; (R)-4,12-bis(diphenylphosphino)-[2,2]-paracyclophane; hydrogen; magnesium oxide; In dichloromethane;

DOI:10.1021/ja028139s

Reference yield:

5-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-4-methyl-pentanoic acid ethyl ester → (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ6-[1,2,3]oxathiazinane-6-carboxylic acid ethyl ester (477200-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ClSO₂NCO; HCO₂H

2: 85 percent / Rh₂(OAc)4; PhI(OAc)2; MgO / CH₂Cl₂

With dirhodium tetraacetate; formic acid; isocyanate de chlorosulfonyle; [bis(acetoxy)iodo]benzene; magnesium oxide; In dichloromethane;

DOI:10.1021/ja028139s

upstream raw materials:

(2R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-sulfamoyloxy-pentanoic acid ethyl ester

ethyl (2R)-4-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-pentenoate

Downstream raw materials:

4-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinane-3,6-dicarboxylic acid 3-tert-butyl ester 6-ethyl ester

6-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5,6-dihydro-4H-pyrimidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

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