(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

Base Information

Chemical Name:(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide
CAS No.:252046-23-4
Molecular Formula:C₃₁H₃₄O₆
Molecular Weight:502.607
Hs Code.:

Synonyms:(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

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Chemical Property of (2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

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Technology Process of (2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

There total 3 articles about (2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide 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: 60.0%

: 252046-22-3
(2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin

: 252046-23-4
(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

: (2R,3R,4S,4aS,7S,8S,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo990389c

Reference yield:

: 252202-48-5
3-(2'-O-prop-1-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene

: 252046-23-4
(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / bis(tricyclohexylphosphine)benzylidene ruthenium(IV) Cl₂ / toluene / 20 °C

2: 60 percent / mCPBA / CH₂Cl₂ / 2 h / 20 °C

With Grubbs catalyst first generation; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; 1: Cyclization / 2: Epoxidation;
DOI:10.1021/jo990389c

Reference yield:

: 161275-25-8
3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

: 252046-23-4
(2R,3R,4S,4aS,7R,8R,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,7,8,9,9a-octahydro-6H-pyrano[3,2-b]oxepin-7,8-epoxide

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 1.33 h

1.2: 87 percent / dimethylformamide / 4 h

2.1: 81 percent / bis(tricyclohexylphosphine)benzylidene ruthenium(IV) Cl₂ / toluene / 20 °C

3.1: 60 percent / mCPBA / CH₂Cl₂ / 2 h / 20 °C

With Grubbs catalyst first generation; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: Cyclization / 3.1: Epoxidation;
DOI:10.1021/jo990389c