3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

Base Information

Chemical Name:3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol
CAS No.:245369-13-5
Molecular Formula:C₃₅H₄₂O₇
Molecular Weight:574.714
Hs Code.:

Synonyms:3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

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Chemical Property of 3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

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Technology Process of 3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

There total 1 articles about 3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol 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: 30.0%

: 557-20-0
diethylzinc

: 115869-43-7
(tert-butyldiphenylsilanyloxy)acetaldehyde

: Acetic acid (E)-3-((2S,3S,4S,5R,6R)-2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-allyl ester

: 3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-1-(tert-butyl-diphenyl-silanyloxy)-pent-4-en-2-ol

: 245369-13-5
3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

Guidance literature:: diethylzinc; (tert-butyldiphenylsilanyloxy)acetaldehyde; Acetic acid (E)-3-((2S,3S,4S,5R,6R)-2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-allyl ester; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 60h;

3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-1-(tert-butyl-diphenyl-silanyloxy)-pent-4-en-2-ol; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(99)01017-5

Reference yield: 68.0%

: 245369-13-5
3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

: 245369-14-6
(2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(1-vinyl-allyloxy)-tetrahydro-pyran

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 20 ℃; for 16h;
DOI:10.1016/S0040-4039(99)01017-5

Reference yield:

: 245369-13-5
3-((2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-pent-4-ene-1,2-diol

: 245369-15-7
(2R,3R,4S,4aS,6S,9aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-vinyl-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocycloheptene

Guidance literature:: Multi-step reaction with 2 steps

1: 68 percent / I₂; PPh₃; imidazole / toluene / 16 h / 20 °C

2: 95 percent / Ru(=CHPh)(PCy₃)2Cl₂ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; iodine; triphenylphosphine; Grubbs catalyst first generation; In dichloromethane; toluene; 1: Deoxygenation / 2: Cyclization;
DOI:10.1016/S0040-4039(99)01017-5