(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(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-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one
• CAS No.: 1309575-66-3
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357
• Mol file: 1309575-66-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(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: 93.0%

(1S,3S,5R)-8,8-dibenzyloxycarbonyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-65-2) → (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-66-3)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at -20 ℃; for 44h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200886j

Reference yield:

(1S,3S,5R)-3-methoxy-8,8-di(methoxycarbonyl)-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-64-1) → (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-66-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With titanium(IV) isopropylate; sodium tetrahydroborate; In tetrahydrofuran; ethanol; benzene;

DOI:10.1021/ol200886j

Reference yield:

(1S,5S)-3-methoxy-8,8-di(methoxycarbonyl)-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane → (1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate; ruthenium(IV) oxide hydrate / 1-Propyl acetate; acetonitrile / 16.5 h / 0 °C / pH 7.4 / aq. phosphate buffer; Inert atmosphere

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

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

With titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; ruthenium(IV) oxide hydrate; In tetrahydrofuran; ethanol; 1-Propyl acetate; acetonitrile; benzene;

DOI:10.1021/ol200886j

upstream raw materials:

(1S,3S,5R)-8,8-dibenzyloxycarbonyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

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

Downstream raw materials:

NPI-2077

(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

(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

(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