(7S,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]-octahydro-indolizin-7-ol

Base Information

Chemical Name:(7S,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]-octahydro-indolizin-7-ol
CAS No.:289659-71-8
Molecular Formula:C₂₉H₄₃NO₄
Molecular Weight:469.665
Hs Code.:

Synonyms:(7S,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]-octahydro-indolizin-7-ol

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Chemical Property of (7S,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]-octahydro-indolizin-7-ol

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Technology Process of (7S,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]-octahydro-indolizin-7-ol

There total 11 articles about (7S,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]-octahydro-indolizin-7-ol 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: 95.0%

: 289659-70-7
(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]-hexahydro-indolizin-7-one

: 289659-71-8
(7S,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]-octahydro-indolizin-7-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol;
DOI:10.1021/ja001440t

Reference yield:

: 123190-88-5
(R)-2-(S)-Pyrrolidin-2-yl-1-(2-trimethylsilanyl-ethoxymethoxy)-propan-2-ol

: 289659-71-8
(7S,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]-octahydro-indolizin-7-ol

Guidance literature:: Multi-step reaction with 8 steps

1: i-Pr₂NEt / tetrahydrofuran

2: 82 percent / KH / tetrahydrofuran

3: 92 percent / NBu₄F / tetrahydrofuran

4: 89 percent / (COCl)2; DMSO; Et₃N

5: 93 percent / Ni(COD)2; PBu₃ / tetrahydrofuran / 18 h / -10 - 0 °C

6: 87 percent / HF*pyridine / tetrahydrofuran

7: 86 percent / (COCl)2; DMSO; Et₃N

8: 95 percent / CeCl₃*7H₂O; NaBH₄ / methanol

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; potassium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1: propargylation / 2: benzylation / 3: deacetalization / 4: Swern oxidation / 5: Cyclization / 6: desilylation / 7: Swern oxidation / 8: Reduction;
DOI:10.1021/ja001440t

Reference yield:

: 123190-87-4
(1R,7aS)-tetrahydro-1-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>methyl-1H,3H-pyrrolo<1,2-c>oxazol-3-one

: 289659-71-8
(7S,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]-octahydro-indolizin-7-ol

Guidance literature:: Multi-step reaction with 9 steps

1: KOH / ethanol

2: i-Pr₂NEt / tetrahydrofuran

3: 82 percent / KH / tetrahydrofuran

4: 92 percent / NBu₄F / tetrahydrofuran

5: 89 percent / (COCl)2; DMSO; Et₃N

6: 93 percent / Ni(COD)2; PBu₃ / tetrahydrofuran / 18 h / -10 - 0 °C

7: 87 percent / HF*pyridine / tetrahydrofuran

8: 86 percent / (COCl)2; DMSO; Et₃N

9: 95 percent / CeCl₃*7H₂O; NaBH₄ / methanol

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tributylphosphine; tetrabutyl ammonium fluoride; potassium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; 1: Hydrolysis / 2: propargylation / 3: benzylation / 4: deacetalization / 5: Swern oxidation / 6: Cyclization / 7: desilylation / 8: Swern oxidation / 9: Reduction;
DOI:10.1021/ja001440t