[(1S)-2-[[(tert-Butyl)diMethylsilyl]oxy]-1-(hydroxyMethyl)ethyl]-carbaMic Acid tert-Butyl Ester

Base Information

• Chemical Name: [(1S)-2-[[(tert-Butyl)diMethylsilyl]oxy]-1-(hydroxyMethyl)ethyl]-carbaMic Acid tert-Butyl Ester
• CAS No.: 185692-85-7
• Molecular Formula: C₁₄H₃₁NO₄Si
• Molecular Weight: 305.49
• Mol file: 185692-85-7.mol

Synonyms:

Chemical Property of [(1S)-2-[[(tert-Butyl)diMethylsilyl]oxy]-1-(hydroxyMethyl)ethyl]-carbaMic Acid tert-Butyl Ester

Chemical Property:

• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

[(1S)-2-[[(tert-Butyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]-carbamicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the synthesis of Chloramphenicol (C325030).

Technology Process of [(1S)-2-[[(tert-Butyl)diMethylsilyl]oxy]-1-(hydroxyMethyl)ethyl]-carbaMic Acid tert-Butyl Ester

There total 3 articles about [(1S)-2-[[(tert-Butyl)diMethylsilyl]oxy]-1-(hydroxyMethyl)ethyl]-carbaMic Acid tert-Butyl Ester 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: 100.0%

(R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester (112418-19-6) → tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate (185692-85-7)

Guidance literature:

(R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester; With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 2.5h;

With ammonium chloride; In tetrahydrofuran; water;

Reference yield:

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) → tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate (185692-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 1 h / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201300977

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate (185692-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 1 h / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201300977

upstream raw materials:

(R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester

tert-butyldimethylsilyl chloride

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

Downstream raw materials:

ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate

(5S)-5-<(tert-butoxycarbonyl)amino>cyclohexadienecarboxylic acid

[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Acetic acid (1R,2R)-3-acetoxy-2-tert-butoxycarbonylamino-1-phenyl-propyl ester

Refernces

• 1、 Ikubo, Masaya,Inoue, Asuka,Nakamura, Sho,Jung, Sejin,Sayama, Misa,Otani, Yuko,Uwamizu, Akiharu,Suzuki, Keisuke,Kishi, Takayuki,Shuto, Akira,Ishiguro, Jun,Okudaira, Michiyo,Kano, Kuniyuki,Makide, Kumiko,Aoki, Junken,Ohwada, Tomohiko. "Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174". supporting information. p. 4204 - 4219. Retrieved 2015/06/08.
• 2、 -. "CYCLIZED DERIVATIVES AS EG-5 INHIBITORS". Page/Page column 68. . Retrieved 2008/12/07.