ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Base Information

Chemical Name:ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate
CAS No.:305322-55-8
Molecular Formula:C₂₅H₃₈N₂O₄Si
Molecular Weight:458.673
Hs Code.:

Synonyms:ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Suppliers and Price of ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 1 raw suppliers

Chemical Property of ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

There total 10 articles about ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate 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: 76.0%

: 198268-14-3
(4S,5R)-4-(2-Benzyloxy-ethyl)-5-[4-(tert-butyl-dimethyl-silanyloxy)-1-methanesulfonyloxy-but-2-ynyl]-4,5-dihydro-pyrazole-1-carboxylic acid ethyl ester

: 305322-55-8
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tributylphosphine; ammonium bicarbonate; In benzene;
DOI:10.1021/jo971571l

Reference yield:

: 124-63-0
methanesulfonyl chloride

: (4S,5R)-4-(2-Benzyloxy-ethyl)-5-[4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-but-2-ynyl]-4,5-dihydro-pyrazole-1-carboxylic acid ethyl ester

: 305322-55-8
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: methanesulfonyl chloride; (4S,5R)-4-(2-Benzyloxy-ethyl)-5-[4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-but-2-ynyl]-4,5-dihydro-pyrazole-1-carboxylic acid ethyl ester; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

With tributylphosphine; ammonium formate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In benzene; at 23 ℃; for 48h;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield:

: 198268-10-9
(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

: 305322-55-8
ethyl (4S,5S)-4-[2-(benzyloxy)ethyl]-5-{4-[(tert-butyl)dimethylsilyloxy]but-2-ynyl}-4,5-dihydropyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: mol. sieves / hexane; CH₂Cl₂ / 90 h / 23 °C

1.2: 71 percent / AgOTf / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

3.1: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: BuMgCl / tetrahydrofuran / 0.5 h / 0 - 23 °C

4.2: tetrahydrofuran / 1 h / 0 - 23 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 2.34 g / HCO₂NH₄; Bu₃P / [Pd₂(dba)3] / benzene / 48 h / 23 °C

With lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; butyl magnesium bromide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Cycloaddition / 1.2: Isomerization / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Metallation / 4.2: Grignard reaction / 5.1: mesylation / 5.2: Hydrogenolysis;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5