9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

Base Information

Chemical Name:9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol
CAS No.:393803-82-2
Molecular Formula:C₄₂H₅₈O₆Si
Molecular Weight:687.004
Hs Code.:

9,10-bis-benzyloxy-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2<i>H</i>,12<i>H</i>-benzo[<i>a</i>]xanthene-12,12a-diol

Synonyms:9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

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Chemical Property of 9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

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Technology Process of 9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

There total 12 articles about 9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol 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: 85.0%

: 393803-75-3
(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

: 393803-82-2
9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

Guidance literature:: With pyridine; hydrogen fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1021/ol016960n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 393803-82-2
9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / pyridine / 1 h / 0 °C

2.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

3.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

4.1: 85 percent / HF; pyridine / tetrahydrofuran / 1.5 h / 20 °C

With pyridine; hydrogen fluoride; tert.-butyl lithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; toluene; pentane;
DOI:10.1021/ol016960n

Reference yield:

: 114626-74-3
(1aR,3aS,5S,7aS,7bS)-5-Acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-82-2
9,10-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,4,6a,11,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H,12H-benzo[a]xanthene-12,12a-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 286 mg / NaOMe / methanol / 22 h / 20 °C

2.1: 86 percent / pyridine / 1 h / 0 °C

3.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

4.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

4.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

5.1: 85 percent / HF; pyridine / tetrahydrofuran / 1.5 h / 20 °C

With pyridine; hydrogen fluoride; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; toluene; pentane;
DOI:10.1021/ol016960n