(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester
CAS No.:247589-99-7
Molecular Formula:C₂₃H₃₆O₆Si
Molecular Weight:436.621
Hs Code.:

Synonyms:(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

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Chemical Property of (2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

There total 10 articles about (2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic 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:

: 17640-15-2
methyl cyanoformate

: 247589-98-6
(2R,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanone

: 247589-99-7
(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

Guidance literature:: (2R,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanone; With lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - -40 ℃;

methyl cyanoformate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at -40 - -20 ℃;
DOI:10.1039/a903160j

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 247589-99-7
(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / imidazole; DMAP

2.1: 100 percent / K₂CO₃ / methanol

3.1: 86 percent / NaH / 0 °C

4.1: 93 percent / DDQ; H₂O / CH₂Cl₂

5.1: 91 percent / (COCl)2; DMSO; Et₃N / -78 °C

6.1: LDA / hexamethylphosphoric acid triamide / -78 - -40 °C

6.2: hexamethylphosphoric acid triamide / -40 - -20 °C

With 1H-imidazole; dmap; oxalyl dichloride; water; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1.1: Etherification / 2.1: Deacetylation / 3.1: Methylation / 4.1: deetheryfication / 5.1: Oxidation / 6.1: Metallation / 6.2: Substitution;
DOI:10.1039/a903160j

Reference yield:

: (3S,5S)-3-Benzyloxymethyl-5-(4-methoxy-benzyloxy)-3-methyl-cyclopentane-1,2-diol

: 247589-99-7
(2S,3S,4R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

2.1: RuCl₃*H₂O; NaIO₄; H₂O / CCl₄; acetonitrile

3.1: dimethylformamide / 40 °C

3.2: H₂SO₄ / tetrahydrofuran

4.1: 96 percent / imidazole; DMAP

5.1: 100 percent / K₂CO₃ / methanol

6.1: 86 percent / NaH / 0 °C

7.1: 93 percent / DDQ; H₂O / CH₂Cl₂

8.1: 91 percent / (COCl)2; DMSO; Et₃N / -78 °C

9.1: LDA / hexamethylphosphoric acid triamide / -78 - -40 °C

9.2: hexamethylphosphoric acid triamide / -40 - -20 °C

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; oxalyl dichloride; water; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Oxidation / 3.1: Substitution / 3.2: Hydrolysis / 4.1: Etherification / 5.1: Deacetylation / 6.1: Methylation / 7.1: deetheryfication / 8.1: Oxidation / 9.1: Metallation / 9.2: Substitution;
DOI:10.1039/a903160j