(R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol

Base Information

• Chemical Name: (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol
• CAS No.: 561055-29-6
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481
• Mol file: 561055-29-6.mol

Synonyms:(R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol

Chemical Property of (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol

There total 6 articles about (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + tert-Butyl ((1R,2R)-2-((benzyloxy)methyl)cyclopropyl)carbamate (561055-28-5) → (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol (561055-29-6)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 7h;

DOI:10.1021/acs.orglett.8b03533

Reference yield:

(-)-(R,R)-2-benzyloxymethylenecyclopropane-1-carboxylic acid (561055-27-4,1932779-15-1) → (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol (561055-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / diphenylphosphoryl azide; triethylamine / 20 h / Heating

2: 95 percent / 4-(N,N-dimethylamino)pyridine / acetonitrile / 48 h / 20 °C

With dmap; diphenylphosphoranyl azide; triethylamine; In acetonitrile;

DOI:10.1021/ol0346887

Reference yield:

(R)-benzyl glycidol (14618-80-5) → (R,R)-O-(benzyl)-{2-[N-(bis-boc)-amino]cyclopropyl}methanol (561055-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / toluene / 0.25 h / 20 °C

1.2: 63 percent / toluene / 14 h / Heating

2.1: 96 percent / sodium hydroxide / ethanol; H₂O / 20 °C

3.1: 53 percent / diphenylphosphoryl azide; triethylamine / 20 h / Heating

4.1: 95 percent / 4-(N,N-dimethylamino)pyridine / acetonitrile / 48 h / 20 °C

With dmap; sodium hydroxide; diphenylphosphoranyl azide; sodium hydride; triethylamine; In ethanol; water; toluene; acetonitrile; 1.2: Wadsworth-Emmons cyclopropanation;

DOI:10.1021/ol0346887

upstream raw materials:

di-tert-butyl dicarbonate

tert-Butyl ((1R,2R)-2-((benzyloxy)methyl)cyclopropyl)carbamate

(R)-benzyl glycidol

(-)-(R,R)-2-benzyloxymethylenecyclopropane-1-carboxylic acid

Downstream raw materials:

(2S,1'S,2'R)-N-(diphenylmethylene)-3-[2-(N-(bis-boc))aminocyclopropyl]alanine tert-butyl ester

(2R,1'S,2'R)-N-(diphenylmethylene)-3-[2-(N-(bis-boc))aminocyclopropyl]alanine tert-butyl ester