Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

Base Information

Chemical Name:Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester
CAS No.:916600-05-0
Molecular Formula:C₃₇H₅₀O₉Si
Molecular Weight:666.884
Hs Code.:

Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

Synonyms:Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

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Chemical Property of Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

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Technology Process of Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

There total 11 articles about Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl 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:

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

: 916600-05-0
Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: 26 mg / pyridine; DMAP / 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

Reference yield:

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

: 916600-05-0
Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 7 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

7.1: 26 mg / pyridine; DMAP / 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:

: (1S,2S,4R,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-1-hydroxy-2-methyl-hept-6-en-3-one

: 916600-05-0
Acetic acid (S)-6-((1R,2R,3R,4R)-2-acetoxy-3,4-bis-benzyloxy-1-methyl-hex-5-enyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 11.0 g / LiBH₄ / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C

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

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

4: 266 mg / citric acid / methanol / 0.5 h / 20 °C

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

6: 26 mg / pyridine; DMAP / 0 - 20 °C

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