2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

Base Information

Chemical Name:2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone
CAS No.:923986-93-0
Molecular Formula:C₄₀H₆₈O₃S₂Si₂
Molecular Weight:717.281
Hs Code.:

Synonyms:2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

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Chemical Property of 2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

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Technology Process of 2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

There total 3 articles about 2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 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%

: 923986-88-3
2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

: 18162-48-6
tert-butyldimethylsilyl chloride

: 923986-93-0
2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ol062319f

Reference yield:

: 923986-89-4
(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane

: 923986-93-0
2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: NCS; AgNO₃ / acetonitrile; H₂O / 0 - 4 °C

1.2: NaBH₄ / acetonitrile; H₂O / 2 h / 20 °C

2.1: 78 percent / BF₃*Et₂O / CHCl₃ / 3 h / 20 °C

3.1: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

With dmap; N-chloro-succinimide; boron trifluoride diethyl etherate; silver nitrate; triethylamine; In dichloromethane; chloroform; water; acetonitrile;
DOI:10.1021/ol062319f

Reference yield:

: 444308-38-7
{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol

: 923986-93-0
2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / BF₃*Et₂O / CHCl₃ / 3 h / 20 °C

2: 95 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

With dmap; boron trifluoride diethyl etherate; triethylamine; In dichloromethane; chloroform;
DOI:10.1021/ol062319f