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

Base Information

Chemical Name:(2R,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanone
CAS No.:247589-98-6
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

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

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

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Technology Process of (2R,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanone

There total 9 articles about (2R,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanone 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: 91.0%

: 247589-97-5
(1S,2S,3S,4S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-cyclopentanol

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -78 ℃;
DOI:10.1039/a903160j

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole; DMAP

2: 100 percent / K₂CO₃ / methanol

3: 86 percent / NaH / 0 °C

4: 93 percent / DDQ; H₂O / CH₂Cl₂

5: 91 percent / (COCl)2; DMSO; Et₃N / -78 °C

With 1H-imidazole; dmap; oxalyl dichloride; water; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; 1: Etherification / 2: Deacetylation / 3: Methylation / 4: deetheryfication / 5: Oxidation;
DOI:10.1039/a903160j

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

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; In methanol; tetrachloromethane; 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;
DOI:10.1039/a903160j