Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

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Chemical Name:Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester
CAS No.:916600-04-9
Molecular Formula:C₃₅H₄₈O₈Si
Molecular Weight:624.847
Hs Code.:

Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

Synonyms:Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

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Chemical Property of Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

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Technology Process of Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

There total 10 articles about Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl 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:

: 916600-03-8
Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(1S,2S)-2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-hydroxy-1-methyl-ethyl}-pent-4-enyl ester

: 916600-04-9
Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

Guidance literature:: With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/ol062234e

Reference yield:

: 916599-82-1
(4R,5R)-4,5-Bis-benzyloxy-hept-6-en-3-one

: 916600-04-9
Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C

1.2: diethyl ether; hexane / 40 h / -15 °C

2.1: 11.0 g / LiBH₄ / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C

3.1: tetrahydrofuran / 0.58 h / -78 - 20 °C

4.1: pyridine; DMAP / CH₂Cl₂ / 18 h / 20 °C

5.1: 266 mg / citric acid / methanol / 0.5 h / 20 °C

6.1: VO(acac)2; tert-butylhydroperoxide / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; lithium borohydride; bis(acetylacetonate)oxovanadium; dicyclohexylboron chloride; triethylamine; citric acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ol062234e

Reference yield:

: 916599-91-2
(4S,5R)-4,5-Bis-benzyloxy-hept-6-en-3-ol

: 916600-04-9
Acetic acid (1R,2R,3R)-2,3-bis-benzyloxy-1-{(R)-1-[(S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / molecular sieves 4 Angstroem; 4-methylmorpholine N-oxide; TPAP / CH₂Cl₂; acetonitrile / 0 - 20 °C

2.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C

2.2: diethyl ether; hexane / 40 h / -15 °C

3.1: 11.0 g / LiBH₄ / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C

4.1: tetrahydrofuran / 0.58 h / -78 - 20 °C

5.1: pyridine; DMAP / CH₂Cl₂ / 18 h / 20 °C

6.1: 266 mg / citric acid / methanol / 0.5 h / 20 °C

7.1: VO(acac)2; tert-butylhydroperoxide / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; lithium borohydride; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; 4 A molecular sieve; dicyclohexylboron chloride; 4-methylmorpholine N-oxide; triethylamine; citric acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/ol062234e