165683-88-5

Basic information

• Product Name: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, [(1S)-1-(2S)-oxiranylethyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 165683-88-5
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• Product Categories: N-BOC
• Mol File: 165683-88-5.mol

Chemical Properties

• Melting Point: 48-50 °C(Solv: dichloromethane (75-09-2); pentane (109-66-0))
• Boiling Point: 272.6±13.0 °C(Predicted)
• Appearance: /
• Density: 1.071±0.06 g/cm3(Predicted)
• PKA: 12.23±0.46(Predicted)
• CAS DataBase Reference: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(165683-88-5)
• EPA Substance Registry System: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(165683-88-5)

Safety Data

• Hazardous Substances Data: 165683-88-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is used as a chiral building block for the development of pharmaceutical compounds. Its unique structure allows for the creation of new drugs with improved efficacy and selectivity, contributing to advancements in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical industry, [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is utilized as a key intermediate in the synthesis of various agrochemical products. Its incorporation aids in the development of more effective and targeted pesticides, herbicides, and other agricultural chemicals.
Used in Organic Synthesis:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is also used as a valuable intermediate in organic synthesis, allowing for the creation of a wide range of organic molecules with diverse applications. Its versatility and reactivity make it an important building block in the field of organic chemistry.
Used in Medicinal Chemistry:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER plays a significant role in medicinal chemistry, where it is employed in the design and synthesis of novel therapeutic agents. Its unique properties enable the development of drugs with improved pharmacological profiles and targeted action against specific diseases.

Upstream product

• 93371-30-3 tert-butyl [(2S)-4-chloro-3-oxobutan-2-yl]carbamate 
• 51814-53-0 N-tert-butoxycarbonyl-L-alanine ethyl ester 
• 545375-08-4 ((1S,2S)-3-Chloro-2-hydroxy-1-methyl-propyl)-carbamic acid tert-butyl ester 
• 178421-71-1 (2S,3S)-3-tert-butoxycarbonylamino-1-tosyloxy-2-butanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 154079-54-6 (2S,3S)-3-tert-butoxycarbonylamino-1,2-butanediol 

Relevant articles and documents

Stereoselective synthesis of anti-N-protected 3-amino-1,2-epoxides by nucleophilic addition to N-tert-butanesulfinyl imine of a glyceraldehyde synthon

(Chemical Equation Presented) A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2- epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

Asymmetric synthesis of ES-285, an anticancer agent isolated from marine sources

The asymmetric synthesis of (2S,3R)-2-amino-3-octane-decanol hydrochloride (ES-285-HC1) was achieved in eight steps in ca. 38% overall yield from the N-benzylimine-derived from. (R)-2,3-O-isopropylidene glyceraldehyde, which is easily available on gram sc

Synthesis and γ-secretase activity of APP substrate-based hydroxyethylene dipeptide isosteres

Two new APP substrate-based hydroxyethylene isosteres (AT and VI) were prepared and their dipeptide conjugates shown not to inhibit the γ-secretase-mediated formation of either Aβ1-40 or Aβ1-42. The FG isostere and a des-hydroxy hydroxyethylene isostere a

A convergent, stereocontrolled synthesis of C2-symmetrical and pseudosymmetrical sulfur-tethered bis(amino alcohols)

The totally enantiocontrolled preparation of C2-symmetrical and pseudosymmetrical sulfur-tethered bis(amino alcohols) from anti-3-amino-1,2- alkane diols is described. The key step in the synthetic procedure involves the use of triphenylsilanethiol as a sulfide or hydrogenosulfide equivalent in the regioselective nucleophilic ring opening of both anti- and syn- aminoalkyl epoxides.

Ready access to stereodefined β-hydroxy-γ-amino acids. Enantioselective synthesis of fully protected cyclohexylstatine

A convenient entry to enantiopure syn or anti β-hydroxy-γ-amino acids is described. The starting compounds for the synthesis, anti 3-amino-1,2-diols, are readily available in high enantiomeric purity through catalytic asymmetric epoxidation of an allylic alcohol and titanium-promoted oxirane opening. After adequate protection of the nitrogen, a stereodivergent sequence leads to both anti and syn N-Boc aminoalkyl epoxides. Subsequent regioselective ring-opening with cyanide, protection of the resulting secondary alcohol and nitrile to carboxyl conversion afford, in good yields, protected β-hydroxy-γ-amino acid belonging to either the anti (erythro) or syn (threo) series. This methodology has been applied to the enantioselective preparation of cyclohexylstatine, a key component of several aspartyl protease inhibitors, in fully protected form.

Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors

Enantiomerically pure N,N-dibenzyl-α-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and high isomeric purity. These compounds are versatile synthetic intermediates for the preparation of hydroxyethylamine-based HIV protease inhibitors, either directly as such, or via conversion to the corresponding N-Boc(2S,3S)-aminoalkyl epoxides. The processes described do not make use of hazardous reagents or intermediates, do not require chromatographic purifications, and are thus amenable to the preparation of large quantities of these versatile building blocks.

A convenient, stereodivergent approach to the enantioselective synthesis of N-Boc-aminoalkyl epoxides

An efficient, stereodivergent and enantioselective synthesis of N-Boc-aminoalkyl epoxides has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-diols, and after a change in the nitrogen protecting group, an intramol