1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

Base Information

Chemical Name:1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane
CAS No.:113668-83-0
Molecular Formula:C₃₁H₃₆O₉S
Molecular Weight:584.687
Hs Code.:

1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

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Chemical Property of 1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

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Technology Process of 1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

There total 2 articles about 1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane 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:

: 105064-21-9
(2S,3R)-rac-2,3-(isopropylidenedioxy)-5-(phenylsulfonyl)-4-cyclopentene

: 113668-82-9
1-(6-Bromo-benzo[1,3]dioxol-5-ylmethyl)-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 106-95-6
allyl bromide

: 113668-83-0
1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

Guidance literature:: With tert.-butyl lithium; Yield given. Multistep reaction; 1.) THF, -78 deg C; 2.) THF/HMPA, -78 deg C;;
DOI:10.1021/ja00215a076

Reference yield:

: (3aS,6aR)-5-Benzenesulfonyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

: 113668-82-9
1-(6-Bromo-benzo[1,3]dioxol-5-ylmethyl)-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 106-95-6
allyl bromide

: 113668-83-0
(3aα,4α,5S*,6aα)-(+/-)-4-methyl-1-<<6--1,3-benzodioxol-5-yl>methyl>-2,6,7-trioxabicyclo<2.2.2>octane

Guidance literature:: Yield given. Multistep reaction;

Reference yield:

: 113668-83-0
1-[6-((3aR,4R,5S,6aS)-5-Allyl-5-benzenesulfonyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-benzo[1,3]dioxol-5-ylmethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 38750-57-1,38848-26-9
(±)-cephalotaxinone

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / t-BuLi / tetrahydrofuran / -78 deg C then room temp.

3: H₂ / 10percent Pd/C / ethanol

4: BH₃ / tetrahydrofuran; methanol / Heating

5: 91 percent / 1N HCl / tetrahydrofuran / Ambient temperature

6: 75 percent / Et₃N, trifluoracetic acid / dimethylsulfoxide; CH₂Cl₂ / -78 °C

7: p-TsOH / dioxane / Heating

With hydrogenchloride; borane; hydrogen; tert.-butyl lithium; triethylamine; trifluoroacetic acid; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja00215a076