tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate
• CAS No.: 1177260-52-4
• Molecular Formula: C₂₅H₃₃NO₄
• Molecular Weight: 411.541
• Mol file: 1177260-52-4.mol

Synonyms:tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate

Chemical Property of tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate

There total 2 articles about tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate 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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,3S,4R)-1-azido-3-benzyloxy-4-benzyloxymethylcyclopentane → tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate (1177260-52-4)

Guidance literature:

With Lindlar's catalyst; hydrogen; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo901127a

Reference yield: 61.0%

benzyl bromide (100-39-0) + tert-butyl-N-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]carbamate (153045-91-1) → tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate (1177260-52-4)

Guidance literature:

tert-butyl-N-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]carbamate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 3.5h;

DOI:10.1002/anie.201904794

Reference yield: 97.0%

tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate (1177260-52-4) + allyl bromide (106-95-6) → tert-butyl allyl((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate (1177260-54-6)

Guidance literature:

tert-butyl ((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate; With potassium hexamethylsilazane; In N,N-dimethyl-formamide; toluene; at -25 ℃; for 0.166667h; Inert atmosphere;

allyl bromide; In N,N-dimethyl-formamide; toluene; at -25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo901127a

upstream raw materials:

di-tert-butyl dicarbonate

benzyl bromide

tert-butyl-N-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]carbamate

Downstream raw materials:

tert-butyl allyl((1R,3S,4R)-3-benzyloxy-4-benzyloxymethylbicyclo[3.1.0]hexan-1-yl)carbamate

(1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane