(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

Base Information

Chemical Name:(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one
CAS No.:256942-73-1
Molecular Formula:C₃₆H₄₀O₄
Molecular Weight:536.711
Hs Code.:

Synonyms:(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

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Chemical Property of (3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

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Technology Process of (3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

There total 7 articles about (3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one 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: 80.0%

: 76-83-5
trityl chloride

: 256942-72-0
(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-benzo[1,3]dioxol-4-one

: 256942-73-1
(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

Guidance literature:: With pyridine; at 20 ℃; for 48h;
DOI:10.1021/jo991225z

Reference yield:

: 155551-04-5
(3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one

: 256942-73-1
(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether; pentane / 1.5 h / -90 °C

1.2: CuCN / diethyl ether; pentane / 0.67 h / -90 - -20 °C

1.3: 37 percent / diethyl ether; pentane / 0.17 h / -80 °C

2.1: 80 percent / pyridine / 48 h / 20 °C

With pyridine; tert.-butyl lithium; In diethyl ether; pentane; 1.1: Metallation / 1.2: Addition / 1.3: Addition / 2.1: Substitution;
DOI:10.1021/jo991225z

Reference yield:

: 200707-80-8
(3aR,4S,7aS)-2,2-Dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-ol

: 256942-73-1
(3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -50 - -10 °C

2.1: t-BuLi / diethyl ether; pentane / 1.5 h / -90 °C

2.2: CuCN / diethyl ether; pentane / 0.67 h / -90 - -20 °C

2.3: 37 percent / diethyl ether; pentane / 0.17 h / -80 °C

3.1: 80 percent / pyridine / 48 h / 20 °C

With pyridine; oxalyl dichloride; tert.-butyl lithium; dimethyl sulfoxide; In diethyl ether; dichloromethane; pentane; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 2.3: Addition / 3.1: Substitution;
DOI:10.1021/jo991225z