(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

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Chemical Name:(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde
CAS No.:388082-00-6
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

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Chemical Property of (2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

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Technology Process of (2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

There total 9 articles about (2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde 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%

: {(2R,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-methanol

: 388082-00-6
(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: With swern reagent;
DOI:10.1021/ol016948v

Reference yield:

: 80910-01-6,108836-41-5,134733-19-0,144069-33-0
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

: 388082-00-6
(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: CuI

2: imidazole

3: OsO₄; NMO

4: NaIO₄

5: DIBAL / -78 °C

6: 90 percent / Ti(O-i-Pr)4; (-)-DET; TBHP / -40 °C

7: 91 percent / Swern reagent

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; N-methyl-2-indolinone; swern reagent; diisobutylaluminium hydride; (-)-diethyl tartrate; 7: Sharpless asymmetric epoxidation / 8: Swern oxidation;
DOI:10.1021/ol016948v

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 388082-00-6
(2S,3R)-3-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole

2: OsO₄; NMO

3: NaIO₄

4: DIBAL / -78 °C

5: 90 percent / Ti(O-i-Pr)4; (-)-DET; TBHP / -40 °C

6: 91 percent / Swern reagent

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; swern reagent; diisobutylaluminium hydride; (-)-diethyl tartrate; 6: Sharpless asymmetric epoxidation / 7: Swern oxidation;
DOI:10.1021/ol016948v