(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

Base Information

Chemical Name:(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
CAS No.:245369-15-7
Molecular Formula:C₃₃H₃₆O₅
Molecular Weight:512.646
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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: 95.0%

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

: 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:: Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 0.5h;
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

Reference yield:

: 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

: 245369-15-7
(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 3 steps

1.1: Pd(PPh₃)4 / tetrahydrofuran / 60 h / 20 °C

1.2: 30 percent / TBAF / tetrahydrofuran / 20 °C

2.1: 68 percent / I₂; PPh₃; imidazole / toluene / 16 h / 20 °C

3.1: 95 percent / Ru(=CHPh)(PCy₃)2Cl₂ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; iodine; triphenylphosphine; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; toluene; 1.1: Alkylation / 1.2: Desilylation / 2.1: Deoxygenation / 3.1: Cyclization;
DOI:10.1016/S0040-4039(99)01017-5