(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde
CAS No.:350046-06-9
Molecular Formula:C₃₀H₄₄O₅Si
Molecular Weight:512.762
Hs Code.:

Synonyms:(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

There total 11 articles about (2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-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: 89.0%

: 350045-93-1
[(2R,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-methanol

: 350046-06-9
(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: [(2R,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-methanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;

With triethylamine; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(01)00530-5

Reference yield:

: 131310-58-2
(2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxirane-2-carbaldehyde

: 350046-06-9
(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / PhCO₂H / benzene / 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

3.1: 78 percent / PPTS / CH₂Cl₂ / 20 °C

4.1: 95 percent / hydrogen / Pd/C / methanol / 20 °C

5.1: 91 percent / LiAlH₄ / diethyl ether / 0 °C

6.1: 90 percent / KH / tetrahydrofuran / 0 °C

7.1: 91 percent / CSA; MeOH / CH₂Cl₂ / 20 °C

8.1: 96 percent / imidazole / dimethylformamide / 70 °C

9.1: 92 percent / CSA; MeOH / CH₂Cl₂ / 0 °C

10.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

10.2: 89 percent / Et₃N / -78 - 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; dimethyl sulfoxide; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Wittig reaction / 10.1: Swern oxidation;
DOI:10.1016/S0040-4039(01)00530-5

Reference yield:

: 350045-95-3
(E)-3-[(2R,3R)-3-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-methyl-oxiranyl]-acrylic acid methyl ester

: 350046-06-9
(2S,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: 78 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 95 percent / hydrogen / Pd/C / methanol / 20 °C

3.1: 91 percent / LiAlH₄ / diethyl ether / 0 °C

4.1: 90 percent / KH / tetrahydrofuran / 0 °C

5.1: 91 percent / CSA; MeOH / CH₂Cl₂ / 20 °C

6.1: 96 percent / imidazole / dimethylformamide / 70 °C

7.1: 92 percent / CSA; MeOH / CH₂Cl₂ / 0 °C

8.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

8.2: 89 percent / Et₃N / -78 - 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 8.1: Swern oxidation;
DOI:10.1016/S0040-4039(01)00530-5