(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Base Information

Chemical Name:(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol
CAS No.:607405-77-6
Molecular Formula:C₃₅H₅₂O₄Si
Molecular Weight:564.881
Hs Code.:

Synonyms:(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

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Chemical Property of (3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

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Technology Process of (3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

There total 17 articles about (3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-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: 100.0%

: 607405-74-3
(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyloxy)methyl]-3,3a,4,6,7,7a-hexahydro-7a-[3-(methoxymethoxy)propyl]-2,3,3,6-tetramethyl-5H-inden-5-one

: 607405-77-6
(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Guidance literature:: With lithium tri(t-butoxy)aluminum hydride; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/jo0301346

Reference yield: 87.0%

: 607405-74-3
(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyloxy)methyl]-3,3a,4,6,7,7a-hexahydro-7a-[3-(methoxymethoxy)propyl]-2,3,3,6-tetramethyl-5H-inden-5-one

: 923570-72-3
(3aR,5R,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

: 607405-77-6
(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/jo062068o

Reference yield:

: 607406-39-3
(1S,2R,4R)-5-[3-(methoxymethoxy)propyl]-1,7,7-trimethylbicyclo[2.2.1]hept-5-en-2-ol

: 607405-77-6
(3aR,5S,6R,7S,7aR)-7-((tert-butyldiphenylsilyloxy)methyl)-7a-(3-(methoxymethoxy)propyl)-2,3,3,6-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-inden-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: 61 percent / tetrahydrofuran; pentane / 4 h / -40 °C

3.1: 1 percent / KHMDS / tetrahydrofuran

4.1: 87 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

With tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; pentane; 1.1: Dess-Martin oxidation / 3.1: oxy-Cope rearrangement;
DOI:10.1021/jo062068o