(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

Base Information

Chemical Name:(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one
CAS No.:859845-18-4
Molecular Formula:C₄₃H₅₀O₆Si
Molecular Weight:690.952
Hs Code.:

Synonyms:(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

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Chemical Property of (2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

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Technology Process of (2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

There total 6 articles about (2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one 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: 95.0%

: 859844-85-2
(2R,4R,5R,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-ol

: 859845-18-4
(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃;
DOI:10.1021/ol051119l

Reference yield:

: 859844-79-4
(2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-triethylsilanyloxy-pentanal

: 859845-18-4
(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: dicyclohexylboron chloride; Et₃N / diethyl ether; hexane / 1.5 h / 0 °C

1.2: 27 percent / diethyl ether; hexane / -78 - -45 °C

2.1: 92 percent / PPh₃*HBr / methanol; tetrahydrofuran / 7 h / 0 °C

3.1: 95 percent / SO₃*Py; Et₃N / CH₂Cl₂; dimethylsulfoxide / 20 °C

With pyridine-SO₃ complex; dicyclohexylboron chloride; triphenylphosphine hydrobromide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol051119l

Reference yield:

: 859845-15-1
(2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-triethylsilanyloxy-pentan-1-ol

: 859845-18-4
(2R,5S,6R)-2-((1S,2S)-1,2-Bis-benzyloxy-but-3-ynyl)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methoxy-5-methyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / Huenigs' base; SO₃*Py / CH₂Cl₂; dimethylsulfoxide / 20 °C

2.1: dicyclohexylboron chloride; Et₃N / diethyl ether; hexane / 1.5 h / 0 °C

2.2: 27 percent / diethyl ether; hexane / -78 - -45 °C

3.1: 92 percent / PPh₃*HBr / methanol; tetrahydrofuran / 7 h / 0 °C

4.1: 95 percent / SO₃*Py; Et₃N / CH₂Cl₂; dimethylsulfoxide / 20 °C

With pyridine-SO₃ complex; dicyclohexylboron chloride; triphenylphosphine hydrobromide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol051119l