(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

Base Information

Chemical Name:(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine
CAS No.:943524-28-5
Molecular Formula:C₂₉H₄₄N₄O₈SSi
Molecular Weight:636.842
Hs Code.:

(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

Synonyms:(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

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Chemical Property of (8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

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Technology Process of (8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

There total 4 articles about (8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine 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: 63.0%

: 943524-27-4
(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

: 98-59-9
p-toluenesulfonyl chloride

: 943524-28-5
(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

Guidance literature:: With pyridine; at 0 - 20 ℃;
DOI:10.1021/ja0708363

Reference yield:

: 943524-26-3
(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-3',5'-di-O-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

: 943524-28-5
(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / NH₃ / methanol / 21 h / 20 - 45 °C

2: 63 percent / pyridine / 0 - 20 °C

With pyridine; ammonia; In methanol;
DOI:10.1021/ja0708363

Reference yield:

: 151256-38-1
(8R)-6-(tert-Butoxycarbonyl)-3-(2'-cyanoethyl)-8-<(tert-butyldimethylsilyl)oxy>-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepine

: 943524-28-5
(8R)-6-(tert-butoxycarbonyl)-8-(tert-butyldimethylsilyloxy)-3-(2'-deoxy-5'-O-tosyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / tBuOK / tetrahydrofuran / 20 °C

2.1: NaH / acetonitrile / 0.5 h

2.2: 85 percent / acetonitrile / 0.67 h

3.1: 71 percent / NH₃ / methanol / 21 h / 20 - 45 °C

4.1: 63 percent / pyridine / 0 - 20 °C

With pyridine; potassium tert-butylate; ammonia; sodium hydride; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/ja0708363