(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

Base Information

Chemical Name:(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate
CAS No.:91156-90-0
Molecular Formula:C₃₂H₄₂O₁₁S
Molecular Weight:634.745
Hs Code.:

(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

Synonyms:(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

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Chemical Property of (+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

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Technology Process of (+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

There total 4 articles about (+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate 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: 74.0%

: 75758-87-1
C₂₅H₃₆O₉

: 98-59-9
p-toluenesulfonyl chloride

: 91156-90-0
(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

Guidance literature:: In pyridine; at 0 ℃;
DOI:10.1021/jo00192a002

Reference yield:

: 91156-88-6
(+/-)-(1α,4bβ,10α)-8,8-(Ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-oxogibb-4a(10a)-ene-10-carboxylic acid

: 91156-90-0
(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / NaBH₄ / ethanol / 0.67 h / 0 °C

2: CH₂Cl₂; diethyl ether / 0.5 h

3: 74 percent / pyridine / 0 °C

With sodium tetrahydroborate; In pyridine; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/jo00192a002

Reference yield:

: 75758-96-2
(+/-)-(1α,4bβ,10α)-8,8-(Ethylenedioxy)-2-methoxy-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methylgibba-2,4a(10a)-diene-10-carboxylic acid

: 91156-90-0
(+/-)-(1α,2α,4bβ,10α)-Ethyl 8,8-(ethylenedioxy)-1-(methoxycarbonyl)-7-<(methoxymethyl)oxy>-1-methyl-2-(4-toluolsulfonyloxy)gibb-4a(10a)-ene-10-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / Hg(NO₃)2 / acetonitrile; H₂O / 18 h / 22 °C

2: 90 percent / NaBH₄ / ethanol / 0.67 h / 0 °C

3: CH₂Cl₂; diethyl ether / 0.5 h

4: 74 percent / pyridine / 0 °C

With sodium tetrahydroborate; mercury(II) nitrate; In pyridine; diethyl ether; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00192a002