(5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Base Information

Chemical Name:(5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one
CAS No.:1379002-60-4
Molecular Formula:C₃₂H₃₆N₂O₅SSi
Molecular Weight:588.8
Hs Code.:

Synonyms:(5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

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Chemical Property of (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

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Technology Process of (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

There total 2 articles about (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-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: 91.0%

: 1379002-57-9
3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

: 103-72-0
phenyl isothiocyanate

: 1379002-60-4
(5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Guidance literature:: 3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose; phenyl isothiocyanate; In tetrahydrofuran; at 20 ℃; for 16h;

With triethylamine; In tetrahydrofuran; at 60 ℃; for 1h;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

: 352541-83-4
5-O-tert-butyldiphenylsilyl-3-C-trichloromethyl-1,2-O-isopropylidene-β-D-lyxofuranose

: 1379002-60-4
(5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium azide; 18-crown-6 ether; 1,8-diazabicyclo[5.4.0]undec-7-ene / 50 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr

3.1: tetrahydrofuran / 16 h / 20 °C

3.2: 1 h / 60 °C

With sodium azide; 18-crown-6 ether; palladium 10% on activated carbon; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; 1.1: modified Corey-Link reaction;
DOI:10.1016/j.tet.2012.03.087