(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

Base Information

Chemical Name:(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal
CAS No.:206272-59-5
Molecular Formula:C₃₉H₅₂O₇Si
Molecular Weight:660.923
Hs Code.:

Synonyms:(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

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Chemical Property of (S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

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Technology Process of (S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

There total 4 articles about (S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal 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%

: 206272-62-0
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-en-1-ol

: 206272-59-5
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; Dess-Martin oxidation;
DOI:10.1016/S0960-894X(98)00050-X

Reference yield:

: 174786-78-8
[(S)-3-Benzenesulfonyl-1-(4-methoxy-benzyloxymethyl)-propoxy]-tert-butyl-dimethyl-silane

: 206272-59-5
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

2: 1.) n-BuLi, 2.) i-PrMgCl / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

3: 86 percent / DDQ / CH₂Cl₂

4: 83 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / Dess-Martin oxidation

With pyridine; n-butyllithium; isopropylmagnesium chloride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1016/S0960-894X(98)00050-X

Reference yield:

: 206272-61-9
tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

: 206272-59-5
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / DDQ / CH₂Cl₂

2: 83 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / Dess-Martin oxidation

With pyridine; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1016/S0960-894X(98)00050-X