Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

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Chemical Name:Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester
CAS No.:306726-06-7
Molecular Formula:C₃₃H₃₇NO₅SSi
Molecular Weight:587.812
Hs Code.:

Synonyms:Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

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Chemical Property of Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

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Technology Process of Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

There total 5 articles about Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-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: 96.0%

: 98-88-4
benzoyl chloride

: 306726-05-6
(R)-[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methanol

: 306726-06-7
Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 2h;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 50622-09-8
2,3-O-isopropylidene-L-threitol

: 306726-06-7
Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 1 h / 0 - 25 °C

1.2: 90 percent / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 4 h / -78 - 0 °C

3.1: CH₂Cl₂ / 12 h / 0 - 25 °C

3.2: PPTS; MeOH / 2 h / 25 °C

4.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

With dmap; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Etherification / 2.1: Oxidation / 3.1: Addition / 3.2: Methanolysis / 4.1: Esterification;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 136032-73-0,127251-09-6
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

: 306726-06-7
Benzoic acid (R)-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-thiazol-2-yl-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 4 h / -78 - 0 °C

2.1: CH₂Cl₂ / 12 h / 0 - 25 °C

2.2: PPTS; MeOH / 2 h / 25 °C

3.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.1: Oxidation / 2.1: Addition / 2.2: Methanolysis / 3.1: Esterification;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8