(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

Base Information

Chemical Name:(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one
CAS No.:1163143-61-0
Molecular Formula:C₂₆H₃₅NO₄SSi
Molecular Weight:485.72
Hs Code.:

Synonyms:(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

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Chemical Property of (1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

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Technology Process of (1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

There total 2 articles about (1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-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: 78.0%

: 1163143-60-9
(1S,5S,6S,8S)-2-benzyl-8-hydroxymethyl-6-phenylthio-3,7-dioxa-2-azabicyclo[3.3.1]-nonan-9-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1163143-61-0
(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1002/chem.201001060

Reference yield: 63.0%

: 1163143-58-5
(3S,4'S)-2-benzyl-3-(2-phenylthio-[1,3]dioxolan-4-yl)-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H-[1,2]oxazine

: 69739-34-0
t-butyldimethylsiyl triflate

: 1163143-61-0
(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

Guidance literature:: (3S,4'S)-2-benzyl-3-(2-phenylthio-[1,3]dioxolan-4-yl)-4-(2-trimethylsilylethoxy)-3,6-dihydro-2H-[1,2]oxazine; t-butyldimethylsiyl triflate; In dichloromethane; at -30 - 20 ℃; for 16h; Inert atmosphere;

With triethylamine; In dichloromethane; at 0 ℃; Inert atmosphere;

With water; ammonium chloride; In dichloromethane;
DOI:10.1002/anie.200805724

Reference yield: 89.0%

: 1163143-61-0
(1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

: 583040-99-7
4-methoxyphenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 1163143-78-9
4-methoxyphenyl 4-O-[(1S,5R,6S,8S)-2-benzyl-8-(tert-butyl(dimethyl)siloxy-methyl)-9-oxo-3,7-dioxa-2-azabicyclo[3.3.1]non-6-yl]-2,3-O-(1-isopropylidene)-α-L-rhamnopyranoside

Guidance literature:: (1S,5S,6S,8S)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one; 4-methoxyphenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside; With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Molecular sieve;
DOI:10.1002/anie.200805724