(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

Base Information

Chemical Name:(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one
CAS No.:1353669-99-4
Molecular Formula:C₃₃H₄₈O₆Si
Molecular Weight:568.826
Hs Code.:

Synonyms:(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

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Chemical Property of (4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

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Technology Process of (4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

There total 11 articles about (4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one 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%

: 1353669-98-3
(1R,2R,3R,4R,4aS,8R,8aS)-2,3-bis(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-1-propyldecahydronaphthalene-1,8,8a-triol

: 1353669-99-4
(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 75 ℃; for 20h; Inert atmosphere;
DOI:10.1002/ejoc.201100815

Reference yield: 50.0%

: 1353669-97-2
(1S,2R,3R,4R,4aR)-2,3-bis(benzyloxy)-4-[(tert-butyldimethylsilyl)-oxy]-1-propyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ol

: 1353669-99-4
(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

: 1353669-98-3
(1R,2R,3R,4R,4aS,8R,8aS)-2,3-bis(benzyloxy)-4-[(tert-butyldimethylsilyl)oxy]-1-propyldecahydronaphthalene-1,8,8a-triol

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 0 ℃; for 24h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201100815

Reference yield:

: 1018784-63-8
C₂₈H₃₂O₅

: 1353669-99-4
(4aS,5R,6R,7R,8R,8aR)-6,7-bis(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]-8,8a-dihydroxy-8-propyloctahydronaphthalen-1(2H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 80 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: [bis(acetoxy)iodo]benzene; iodine / cyclohexane / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / Inert atmosphere; Reflux

5.1: potassium carbonate / methanol; dichloromethane / 0 °C / Inert atmosphere

6.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / Inert atmosphere

7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 0 °C / Inert atmosphere

With 1H-imidazole; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; iodine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1002/ejoc.201100815