(R)-3-tert-butyldimethylsilanyloxy-4-phenoxy-1-butyne

Base Information

• Chemical Name: (R)-3-tert-butyldimethylsilanyloxy-4-phenoxy-1-butyne
• CAS No.: 149862-37-3
• Molecular Formula: C16H24O2Si
• Molecular Weight: 276.451
• DSSTox Substance ID: DTXSID101142109
• Mol file: 149862-37-3.mol

Synonyms:SCHEMBL6137275;KXGZTYHMLQHERX-CQSZACIVSA-N;DTXSID101142109;(R)-3-tert-butyldimethylsilanyloxy-4-phenoxy -1-butyne;Silane, (1,1-dimethylethyl)dimethyl[[(1R)-1-(phenoxymethyl)-2-propynyl]oxy]-;149862-37-3

Chemical Property of (R)-3-tert-butyldimethylsilanyloxy-4-phenoxy-1-butyne

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 276.154556538
• Heavy Atom Count: 19
• Complexity: 315

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC(COC1=CC=CC=C1)C#C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H](COC1=CC=CC=C1)C#C

Technology Process of (R)-3-tert-butyldimethylsilanyloxy-4-phenoxy-1-butyne

There total 1 articles about (R)-3-tert-butyldimethylsilanyloxy-4-phenoxy-1-butyne 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-4-phenoxy-1-butyn-3-ol → (R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne (149862-37-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1h;

DOI:10.1021/jo00066a020

Reference yield:

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne (149862-37-3) → (dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester (73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-Bu₃SnH, AIBN

2: 61 percent / HF / tetrahydrofuran

With 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran;

DOI:10.1039/c39940001251

Reference yield:

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6) + (R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne (149862-37-3) → (3R,4R)-2-methylene-3-[(3R)-3-(t-butyldimethylsiloxy)-4-phenoxy-1-butynyl]-4-(t-butyldimethylsiloxy)cyclopentan-1-one

Guidance literature:

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne; With n-butyllithium; In hexane; toluene; for 0.5h;

With diethylaluminium chloride; In hexane; at 20 ℃; for 0.5h;

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol; In toluene; at 20 ℃; for 0.25h;

DOI:10.1016/S0968-0896(99)00288-6

upstream raw materials:

tert-butyldimethylsilyl chloride

Downstream raw materials:

(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

Refernces

• 1、 Gooding, Owen W.,Beard, Colin C.,Cooper, Gary F.,Jackson, David Y.. "Triply Convergent Synthesis of 15-(Phenoxymethyl) and 4,5-Allenyl Prostaglandins. Preparation of an Individual Isomer of Enprostil". . p. 3681 - 3686. Retrieved 2007/10/02.