Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

Base Information

Chemical Name:Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate
CAS No.:79069-64-0
Molecular Formula:C₁₈H₂₁BrO₅
Molecular Weight:397.266
Hs Code.:

Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiro<bicyclo<2.2.1>heptane-2,2'-<1,3>dioxolane>-7-carboxylate

Synonyms:Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

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Chemical Property of Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

Chemical Property:

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Technology Process of Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

There total 1 articles about Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-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:

: 100-39-0
benzyl bromide

: 79120-26-6
Methyl (+)-(1α,4α,5α,7R*)-5-bromo-7-hydroxyspiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

: 79069-64-0
Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

Guidance literature:: With sodium hydride; Yield given. Multistep reaction; 1) benzene, DMSO, 1.5 h, 65 deg C, 2) 18 h, 65 deg C;
DOI:10.1021/jo00337a039

Reference yield:

: 79069-64-0
Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

: 79069-69-5
(1α,4α,5α,7R*)-5-Bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-methanol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 6h;
DOI:10.1021/jo00337a039

Reference yield:

: 79069-64-0
Methyl (-)-(1α,4α,5α,7R*)-5-bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-carboxylate

: 79069-65-1
(-)-<1α,4α,5α,7R*,(E)>-5-Bromo-7-(benzyloxy)spiroheptane-2,2'-<1,3>dioxolane>-7-yl-3(S*)-acetoxy-1-octene

Guidance literature:: Multi-step reaction with 5 steps

1: 1.06 g / LiAlH₄ / diethyl ether / 6 h / 25 °C

2: 95 percent / CrO₃, pyridine / CH₂Cl₂ / 0.33 h / 25 °C

3: 1) n-BuLi / 1) heptane, hexane, 1 h, -78 deg C, 2) THF, 1 h, 0 deg C

4: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h

5: 77 percent / PdCl₂(MeCN)2 / tetrahydrofuran / 24 h

With pyridine; chromium(VI) oxide; dmap; lithium aluminium tetrahydride; n-butyllithium; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00337a039