(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Base Information

Chemical Name:(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene
CAS No.:244770-83-0
Molecular Formula:C₂₅H₂₈O₆
Molecular Weight:424.494
Hs Code.:

Synonyms:(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

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Chemical Property of (2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

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Technology Process of (2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

There total 15 articles about (2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 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: 84.0%

: 100-39-0
benzyl bromide

: 440320-29-6
(2R,4aR,5aS,10aR,11R,11aS)-2-(4-Methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-ol

: 244770-83-0
(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(02)00041-8

Reference yield: 21.0%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 100-39-0
benzyl bromide

: 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

: 244770-83-0
(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

: (2R,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-6-((Z)-but-2-enyl)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: (2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin; With ammonia; sodium; In tetrahydrofuran; ethanol; at -78 ℃; for 2h;

p-Anisaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

benzyl bromide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(02)00041-8

Reference yield:

: 13265-84-4
D-glucal

: 244770-83-0
(2R,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-2-(4-methoxy-phenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: NaH / dimethylformamide / 0 - 20 °C

3: NBS; H₂O / tetrahydrofuran

4: KHMDS; 18-crown-6 / toluene / 4 h / -75 - 0 °C

5: 0 - 20 °C

6: 93 percent / NaH / 0 - 20 °C

7: 94 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

8: PPTS / CH₂Cl₂

With pyridine; N-Bromosuccinimide; 18-crown-6 ether; water; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: Etherification / 3: Addition / 4: Dehydrobromination / 5: Addition / 6: Etherification / 7: Cyclization / 8: Etherification;
DOI:10.1039/a903063h