((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol

Base Information

• Chemical Name: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol
• CAS No.: 142096-80-8
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.258
• Mol file: 142096-80-8.mol

Synonyms:(-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane

Chemical Property of ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol

There total 18 articles about ((1R,2R)-2-(benzyloxyMethyl)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: 98.0%

trans-1-benzyloxy-4-trityloxy-2,3-methanobutane → (-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane (142096-80-8) + ((1S,2S)-2-((benzyloxy)methyl)cyclopropyl) methanol

Guidance literature:

With hydrogenchloride; In methanol; for 12h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4020(95)00760-6

Reference yield: 85.0%

(-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane (52745-75-2) + benzyl chloride (100-44-7) → (-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane (142096-80-8)

Guidance literature:

(-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 60 ℃; Inert atmosphere;

benzyl chloride; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1039/b812777h

Reference yield:

(R)-benzyl glycidol (14618-80-5) → (-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane (142096-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 95.5 percent / copper(I) iodide / tetrahydrofuran / -78 - 0 °C

2: 99 percent / imidazole / dimethylformamide / 20 °C

3: 85 percent / Grubb's catalyst / CH₂Cl₂ / Heating

4: tetrahydrofuran / 0.25 h

5: 2,6-lutidine; Tf₂O / CH₂Cl₂ / 0.08 h / -78 °C

6: OsO₄; NaIO₄

7: NaBH₄

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; trifluoromethylsulfonic anhydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0037163

upstream raw materials:

(E)-4-(benzyloxy)-2-buten-1-ol

bis(iodomethyl)zinc

diiodomethane

(1R,2R)-2-((benzyloxy)methyl)cyclopropanecarbaldehyde

Downstream raw materials:

(-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane

(1R,2R)-2-((benzyloxy)methyl)cyclopropanecarbaldehyde

2-methylsulfonyloxymethylene cyclopropylmethyl benzyl ether

2-fluoromethylene cyclopropylmethyl benzyl ether