(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Base Information

Chemical Name:(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one
CAS No.:1309575-68-5
Molecular Formula:C₂₈H₃₇NO₈
Molecular Weight:515.604
Hs Code.:

(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Synonyms:(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

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Chemical Property of (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

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Technology Process of (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

There total 8 articles about (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-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:

: 1309575-76-5
(1S,3S,5R,8S)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-formyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 112520-99-7,1177092-71-5
tributyl(cyclohex-2-en-1-yl)stannane

: 1309575-69-6
(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 1309575-68-5
(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Guidance literature:: With n-butyllithium; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 5h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol200886j

Reference yield:

: 1309575-64-1
(1S,3S,5R)-3-methoxy-8,8-di(methoxycarbonyl)-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 1309575-69-6
(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 1309575-68-5
(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Guidance literature:: Multi-step reaction with 7 steps

1: titanium(IV) isopropylate / benzene / 12 h / 20 - 130 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran; ethanol / 44 h / -20 °C / Inert atmosphere

3: acetonitrile / 1 h / 20 °C / Inert atmosphere

4: dmap / acetonitrile / 12 h / 0 °C / Inert atmosphere

5: camphor-10-sulfonic acid / methanol / 3 h / 0 °C / Inert atmosphere

6: Dess-Martin periodane / dichloromethane / 45 h / 20 °C / Inert atmosphere

7: n-butyllithium; zinc(II) chloride / tetrahydrofuran; hexane / 5 h / -78 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ol200886j

Reference yield:

: 1309575-67-4
(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-hydroxymethyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 1309575-69-6
(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

: 1309575-68-5
(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 45 h / 20 °C / Inert atmosphere

2: n-butyllithium; zinc(II) chloride / tetrahydrofuran; hexane / 5 h / -78 °C / Inert atmosphere

With n-butyllithium; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol200886j