(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
CAS No.:679812-26-1
Molecular Formula:C₃₅H₄₆O₆Si
Molecular Weight:590.832
Hs Code.:

Synonyms:(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Chemical Property of (2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Technology Process of (2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

There total 13 articles about (2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-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: 83.0%

: (3R,4R)-3-Benzyloxy-2-[(2S,4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-4-methyl-tetrahydro-pyran-2-ol

: 149-73-5
trimethyl orthoformate

: 679812-26-1
(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 21 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

: 679812-24-9
(2R,3R)-2-Benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-pentanal

: 679812-26-1
(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 71 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.67 h / -78 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

2.2: 98 percent / Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

3.1: 70 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

4.1: 83 percent / CSA / methanol / 2 h / 21 °C

With oxalyl dichloride; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; camphor-10-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; 2.1: Swern oxidation;
DOI:10.1016/j.tetlet.2005.05.062

Reference yield:

: (R)-4-[(R)-3-(4-Methoxy-benzyloxy)-1-methyl-propyl]-2-phenyl-[1,3]dioxolane

: 679812-26-1
(2R,3R,5S)-5-((2R,3R,4R)-3-Benzyloxy-2-methoxy-4-methyl-tetrahydro-pyran-2-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 74 percent / DIBALH / benzene / 1.5 h / 0 °C

2.1: 97 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 71 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.67 h / -78 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 98 percent / Et₃N / CH₂Cl₂ / 0.33 h / -78 - 0 °C

5.1: 70 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

6.1: 83 percent / CSA / methanol / 2 h / 21 °C

With oxalyl dichloride; dimethyl pimelimidate dihydrochloride; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; benzene; 2.1: Dess-Martin oxidation / 4.1: Swern oxidation;
DOI:10.1016/j.tetlet.2005.05.062