(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Base Information

• Chemical Name: (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate
• CAS No.: 1204748-26-4
• Molecular Formula: C₄₃H₅₁NO₇Si
• Molecular Weight: 721.966
• Mol file: 1204748-26-4.mol

Synonyms:(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Chemical Property of (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

There total 1 articles about (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate 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%

(R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxybutyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (1204748-25-3) → (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1204748-26-4)

Guidance literature:

With oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 2h;

DOI:10.1021/jo902355p

Reference yield: 94.0%

(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1204748-26-4) + methanesulfonyl chloride (124-63-0) → (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2S,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-(methylsulfonyloxy)butyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1204748-27-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo902355p

Reference yield:

(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-hydroxybutyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1204748-26-4) + 4-nitro-benzoic acid (62-23-7) → (1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2S,3R)-1,2-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(4-nitrobenzoyloxy)butyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1204748-44-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20 ℃;

DOI:10.1021/jo902355p

upstream raw materials:

(R)-(9H-fluoren-9-yl)methyl 2-((1R,2R,3S)-1,2-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxybutyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Downstream raw materials:

(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2S,3S)-1,2-bis(benzyloxy)-4-(tertbutyldimethylsilyloxy)-3-(methylsulfonyloxy)butyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

(1S,2S,5R)-(9H-fluoren-9-yl)methyl 2-((1R,2S,3R)-1,2-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(4-nitrobenzoyloxy)butyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate