<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

Base Information

• Chemical Name: <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol
• CAS No.: 134756-63-1
• Molecular Formula: C₁₉H₃₀O₃Si
• Molecular Weight: 334.531
• Mol file: 134756-63-1.mol

Synonyms:<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

Chemical Property of <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

There total 8 articles about <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol 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: 60.0%

((1S,2S,3S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-3-yloxy)-tert-butyl-dimethyl-silane (668996-12-1) → <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol (134756-63-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; Heating;

DOI:10.1016/j.tetlet.2003.11.052

Reference yield:

Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester (174810-43-6) → <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol (134756-63-1)

Guidance literature:

With ammonia; In methanol; Yield given;

DOI:10.1021/ja00015a051

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → <1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol (134756-63-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / triethylamine, DMAP / CH₂Cl₂ / 1 h

2: 95 percent / NaH₂PO₄ buffer, aq. sodium azide / 144 h / electric eel acetylcholinesterase

3: imidazole / 0.5 h

4: methanolic ammonia / 48 h

With 1H-imidazole; dmap; sodium azide; NaH₂PO₄ buffer; ammonia; triethylamine; In dichloromethane;

DOI:10.1021/ja960526c

upstream raw materials:

Acetic acid (1R,4S,5S)-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester

((1S,2S,3S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-3-yloxy)-tert-butyl-dimethyl-silane

(1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane

tert-butyldimethylsilyl chloride

Downstream raw materials:

<1R-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethysilyl)oxy>-1-O-(dimethylamidino)-2-cyclopentene

<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,6a-dihydro-N,N-dimethyl-6H-cyclopentoxazol-2-amine

<1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate