(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

Base Information

Chemical Name:(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol
CAS No.:172268-61-0
Molecular Formula:C₂₇H₃₈O₄Si
Molecular Weight:454.682
Hs Code.:

Synonyms:(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

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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 (2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

There total 13 articles about (2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol 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: 74.0%

: 172268-40-5
(E)-(S)-4-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-2-methyl-pent-3-en-1-ol

: 172268-61-0
(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: With toluene-4-sulfonic acid; In 1,2-dimethoxyethane; Heating;
DOI:10.1021/ja00153a031

Reference yield:

: 172587-76-7
(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

: 172268-61-0
(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

2: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature

3: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

4: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

5: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

6: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

With pyridine; quinoline; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; magnesium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja972497r

Reference yield:

: 1-[(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

: 172268-61-0
(2S,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-4-hydroxy-1,3-dimethyl-but-1-enyl)-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature

2: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h

3: 95 percent / H₂, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h

4: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h

5: 74 percent / p-toluenesulfonic acid / dimethylformamide; H₂O / 24 h / Heating

With pyridine; quinoline; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; magnesium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja972497r