(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

Base Information

Chemical Name:(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine
CAS No.:144766-10-9
Molecular Formula:C₂₉H₄₃NO₄
Molecular Weight:469.665
Hs Code.:

Synonyms:(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

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Chemical Property of (7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

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Technology Process of (7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

There total 36 articles about (7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine 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: 87.0%

: 289659-69-4
(7R,8R,8aS)-8-Benzyloxy-8-methyl-6-[(E)-(R)-2-methyl-5-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-4-en-(E)-ylidene]-7-triethylsilanyloxy-octahydro-indolizine

: 144766-10-9
(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1021/ja001440t

Reference yield: 79.0%

: 144735-52-4
(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

: 144766-10-9
(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

Guidance literature:: With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/ja00052a081

Reference yield:

: 91550-08-2
(S)-2-acetylpyrrolidine-1-carboxylic acid tert-butyl ester

: 144766-10-9
(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

Guidance literature:: Multi-step reaction with 15 steps

1: CH₂Cl₂ / Ambient temperature

2: 1.) BuLi / 1.) hexane, THF, -30 deg C to -20 deg C, 1.5 h, 2.) hexane, THF, -78 deg C, 30 min

3: 68 percent / Hg(ClO₄)2*3H₂O / CHCl₃ / 3 h / Ambient temperature

4: 89 percent / Et₃N / tetrahydrofuran / 2.5 h / Ambient temperature

5: 91 percent / KH / tetrahydrofuran / 2 h / Heating

6: 95 percent / AgNO₃ / ethanol / 1 h / Ambient temperature

7: 79 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 99 percent / 3 N aq. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

9: 98 percent / NaBH₄ / methanol / 1 h / Ambient temperature

10: 94 percent / imidazole, DMAP / dimethylformamide / 1 h / Ambient temperature

11: 85 percent / H₂ / 10percent Pd/C / methanol / 0.08 h / 760 Torr

12: 70 percent / i-Pr₂NEt / tetrahydrofuran / 48 h / Ambient temperature

13: 94 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

14: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, from -78 deg C to RT

15: 79 percent / CrCl₂, NiCl₂ / dimethylformamide / 40 h / Ambient temperature

With 1H-imidazole; chromium dichloride; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;