(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

Base Information

• Chemical Name: (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane
• CAS No.: 87154-05-0
• Molecular Formula: C₁₈H₂₂N₂O₇S
• Molecular Weight: 410.448

Synonyms:(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

Chemical Property of (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

Chemical Property:

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Technology Process of (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

There total 2 articles about (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane 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: 94.0%

(+)-(5R,7R,8S)-8-(1-hydroxymethyl)-2,2,5-trimethyl-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (87154-06-1) + 4-nitrobenzyl chloroformate (4457-32-3) → (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (87154-05-0)

Guidance literature:

With dmap; In dichloromethane; 1.) -4 deg C, 2.) 5 deg C, 24 h;

DOI:10.1055/s-1992-26329

Reference yield:

(+)-(5R,7R)-2,2,5-trimethyl-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (78560-84-6) → (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (87154-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi, diisopropylamine / 1.) THF, hexane, -75 deg C, 2.) -75 deg C, 60 min

2: 94 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 1.) -4 deg C, 2.) 5 deg C, 24 h

With dmap; n-butyllithium; diisopropylamine; In dichloromethane;

DOI:10.1055/s-1992-26329

Reference yield: 70.0%

(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (87154-05-0) → (+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane-6,6-dioxide (87154-04-9,146142-26-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -5 - 5 ℃; for 4.5h;

DOI:10.1055/s-1992-26329

upstream raw materials:

(+)-(5R,7R,8S)-8-(1-hydroxymethyl)-2,2,5-trimethyl-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

4-nitrobenzyl chloroformate

(+)-(5R,7R)-2,2,5-trimethyl-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

Downstream raw materials:

(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane-6,6-dioxide

(+)-(3S,4R)-4-<(2R)-2-(1-hydroxypropyl)-sulfonyl>-3-(p-nitrobenzyloxycarbonyloxymethyl)azetidin-2-one

p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)-4-methylthio-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)- and (3S,4S)-4-chloro-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

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