tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate
• CAS No.: 168960-18-7
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.27300
• European Community (EC) Number: 815-078-9
• Nikkaji Number: J732.498G
• Wikidata: Q76416546
• Mol file: 168960-18-7.mol

Synonyms:168960-18-7;tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate;tert-butyl (1r,4s)-4-(hydroxymethyl)cyclopent-2-enylcarbamate;TERT-BUTYL N-[(1R,4S)-4-(HYDROXYMETHYL)CYCLOPENT-2-EN-1-YL]CARBAMATE;SCHEMBL5016759;Carbamic acid, N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester;DS-15070;C73251;A882130;(1R,4S)-N-BOC-1-amino-4-(hydroxy-methyl)-2-cyclopentene;(1R, 4S)-N-BOC-1-amino-4-(hydroxy-methyl)-2-cyclopentene;4beta-(Hydroxymethyl)-2-cyclopenten-1beta-ylcarbamic acid tert-butyl ester;[(1R,4S)-4-(Hydroxymethyl)-2-cyclopenten-1-yl]-carbamic acid,1,1-dimethylethyl ester;TERT-BUTYL CIS[(4S)-(HYDROXYMETHYL)CYCLOPENT-2-EN-1(R)-YL]CARBAMATE

Chemical Property of tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

Chemical Property:

• Boiling Point: 338.8±31.0 °C(Predicted)
• PKA: 12.06±0.40(Predicted)
• PSA: 58.56000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 1.83900
• Storage Temp.: 2-8°C
• Solubility.: DMSO; Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

N-?[(1R,?4S)?-?4-?(Hydroxymethyl)?-?2-?cyclopenten-?1-?yl]?-carbamicAcid1,?1-?DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CC(C=C1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1C[C@@H](C=C1)CO
• Uses: N-?[(1R,?4S)?-?4-?(Hydroxymethyl)?-?2-?cyclopenten-?1-?yl]?-carbamic Acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing ent-Abacavir (Abacavir EP Impurity A) (A105015), an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Technology Process of tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

There total 50 articles about tert-butyl ((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate 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%

di-tert-butyl dicarbonate (24424-99-5) + (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride (168960-19-8,287717-44-6) → (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene (168960-18-7,172720-97-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; for 4h;

DOI:10.1021/jo00119a044

Reference yield: 97.0%

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (151792-53-9) → (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene (168960-18-7,172720-97-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ja050732x

Reference yield: 88.0%

tert-butyldicarbonate (34619-03-9) + (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) → (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene (168960-18-7,172720-97-7)

Guidance literature:

(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one; With methanesulfonic acid; In tetrahydrofuran; water; at 34 - 44 ℃; for 2.75h; Heating / reflux;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 18.5h; Heating / reflux;

tert-butyldicarbonate; With sodium fluoride; more than 3 stages;

upstream raw materials:

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

di-tert-butyl dicarbonate

(1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate

Downstream raw materials:

(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene

(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5',O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine

Refernces

• 1、 Wehn, Paul M.,Bois, J. Du. "A stereoselective synthesis of the bromopyrrole natural product (-)-Agelastatin a". supporting information; experimental part. p. 3802 - 3805. Retrieved 2009/09/25.
• 2、 Kudoh, Takashi,Fukuoka, Masayoshi,Ichikawa, Satoshi,Murayama, Takashi,Ogawa, Yasuo,Hashii, Minako,Higashida, Haruhiro,Kunerth, Svenja,Weber, Karin,Guse, Andreas H.,Potter, Barry V. L.,Matsuda, Akira,Shuto, Satoshi. "Synthesis of stable and cell-type selective analogues of cyclic ADP-ribose, a Ca2+-mobilizing second messenger. Structure-activity relationship of the N1-ribose moiety". . p. 8846 - 8855. Retrieved 2007/10/03.