(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester
CAS No.:270070-83-2
Molecular Formula:C₂₃H₃₆O₆Si
Molecular Weight:436.621
Hs Code.:

(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

There total 26 articles about (3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic 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:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: (3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-methoxy-2-methoxymethoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

: 270070-83-2
(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: O-benzyl 2,2,2-trichloroacetimidate; (3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-methoxy-2-methoxymethoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester; With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃;

With trifluorormethanesulfonic acid; In dichloromethane;
DOI:10.1016/S0040-4039(00)00013-7

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: (3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-methoxy-2-methoxymethoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

: 270070-83-2
(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

: (3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-2-methoxymethoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(00)00013-7

Reference yield:

: (S)-2-[(3aR,5S,6R,6aR)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanol

: 270070-83-2
(3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: pyridine

2.1: O₃; Ph₃P / methanol / -78 °C

3.1: NaBH₄ / methanol

4.1: 2,6-lutidine / CH₂Cl₂

5.1: DIBAL-H / CH₂Cl₂ / -78 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: NaClO₂; aq. NH₂SO₃H; aq. Na₂HPO₄ / 2-methyl-propan-2-ol

8.1: diethyl ether; CH₂Cl₂ / 0 °C

9.1: potassium hexamethyldisilazide / tetrahydrofuran / -78 °C

10.1: DMAP / pyridine

11.1: AcOH; H₂O / tetrahydrofuran

12.1: pyridine

13.1: 92 percent / aq. TFA / 0 °C

14.1: NaIO₄ / methanol; H₂O

15.1: BF₃*Et₂O / CH₂Cl₂ / 0 °C

16.1: MeOH; NEt₃

17.1: Raney Ni T-4 / acetone / Heating

18.1: 2,6-lutidine / CH₂Cl₂

19.1: aq. NH₃ / methanol

20.1: iPr₂NEt / CHCl₃

21.1: NaOMe / methanol

22.1: TfOH / CH₂Cl₂ / 0 °C

22.2: TfOH / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; methanol; dmap; ammonium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; oxalyl dichloride; trifluorormethanesulfonic acid; Raney Ni T-4; boron trifluoride diethyl etherate; aminosulfonic acid; water; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; acetone; tert-butyl alcohol; 1.1: Acylation / 2.1: ozonolysis / 3.1: Reduction / 4.1: silylation / 5.1: deesterification / 6.1: Oxidation / 7.1: Oxidation / 8.1: Methylation / 9.1: Dieckmann cyclization / 10.1: Acylation / 11.1: Hydrolysis / 12.1: Acetylation / 13.1: Hydrolysis / 14.1: Ring cleavage / 15.1: dithioacetalization / 16.1: methanolysis / 17.1: Elimination / 18.1: silylation / 19.1: Hydrolysis / 20.1: Etherification / 21.1: Deacetylation / 22.1: benzylation / 22.2: deetherification;
DOI:10.1016/S0040-4039(00)00013-7