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

Base Information

Chemical Name:(5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one
CAS No.:1379002-71-7
Molecular Formula:C₁₆H₁₈N₂O₅S
Molecular Weight:350.395
Hs Code.:

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

There total 5 articles about (5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-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: 81.0%

: 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

: 1379002-71-7
(5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

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

: 1379002-71-7
(5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 16 h / 20 °C

1.2: 1 h / 60 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

: 172751-32-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

: 1379002-71-7
(5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

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

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

4.1: tetrahydrofuran / 16 h / 20 °C

4.2: 1 h / 60 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With sodium azide; 18-crown-6 ether; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 2.1: modified Corey-Link reaction;
DOI:10.1016/j.tet.2012.03.087