(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

Base Information

Chemical Name:(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol
CAS No.:326494-36-4
Molecular Formula:C₅₀H₇₄O₅Si₄
Molecular Weight:867.477
Hs Code.:

(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

Synonyms:(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

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Chemical Property of (E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

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Technology Process of (E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

There total 5 articles about (E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-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%

: 326494-35-3
(S)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-penta-1,4-diyn-3-ol

: 326494-36-4
(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at -15 ℃;
DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

: 1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-penta-1,4-diyn-3-ol

: 326494-36-4
(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / montmorillonite K 10; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

2: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran / -78 °C

3: 83 percent / Red-Al / diethyl ether / -15 °C

With n-butyllithium; 4 A molecular sieve; Montmorillonite K 10; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; 2: acetal <1,2> Wittig rearrangement;
DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

: (3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one

: 326494-36-4
(E)-(R)-3-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-1-(tert-butyl-diphenyl-silanyl)-5-trimethylsilanyl-pent-1-en-4-yn-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / diethyl ether / -78 °C

2: 80 percent / montmorillonite K 10; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

3: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran / -78 °C

4: 83 percent / Red-Al / diethyl ether / -15 °C

With n-butyllithium; 4 A molecular sieve; Montmorillonite K 10; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; 3: acetal <1,2> Wittig rearrangement;
DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K