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Cas Database

100021-11-2

100021-11-2

Identification

  • Product Name:(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

  • CAS Number: 100021-11-2

  • EINECS:

  • Molecular Weight:220.268

  • Molecular Formula: C13H16O3

  • HS Code:

  • Mol File:100021-11-2.mol

Synonyms:(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

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Relevant articles and documentsAll total 4 Articles be found

Chemo-enzymatic synthesis of tetra-N-acetyl-chitotetraosyl allosamizoline

Huang, Gang-Liang,Mei, Xin-Ya,Zhang, Hou-Cheng,Wang, Peng-George

, p. 2860 - 2861 (2008/09/20)

A new compound 7, possessing a tetra-N-acetyl-chitotetraosyl moiety as a constituent, was synthesized by bacterial fermentation which used allosamizoline 6 as the initial acceptor.

Template-directed synthesis of (±)-allosamizoline and its 3,4-epimers

Trost, Barry M.,Van Vranken, David L.

, p. 1261 - 1263 (2007/10/02)

-

Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals

-

, (2008/06/13)

Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.

A Novel and Stereospecific Synthesis of (+/-)- and (-)-Aristeromycin

Madhavan, G. V. Bindu,Martin, John C.

, p. 1287 - 1293 (2007/10/02)

A new, efficient synthetic route to (+/-)- and (-)-aristeromycin (1) has been developed which has as its key feature the cycloaddition of singlet oxygen to 5--1,3-cyclopentadiene (8) followed by in situ reduction to give ene diol 10.This reaction has been optimized and scaled-up to give 197 g (60percent) of partially purified 10.The key intermediate azide 15 was prepared from the partially purified 10 in 56percent yield by a three-step sequence of epoxidation to give 13, reaction with NaN3, and acetonation.Azide 15 was converted by standard chemistry via adenine intermediate 22 to (+/-)-aristeromycin (1) in 31percent overall yield.Intermediate 22 was also prepared in 25percent yield by a novel and shorter sequence which involved the reaction of epoxide 13 with the sodium salt of adenine and then acetonation.Alternatively, azide 15 was resolved by conversion to its naproxen ester 26, and the (-)-isomer of 15 was converted to the known amino triol 31, thus constituting a formal synthesis of (-)-aristeromycin.

Process route upstream and downstream products

Process route

thallium cyclopentadiene

thallium cyclopentadiene

Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

aqueous Na2 Cr2 O7

aqueous Na2 Cr2 O7

rose bengal
24545-87-7

rose bengal

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Conditions
Conditions Yield
With sodium acetate; thiourea; In methanol; ethyl acetate;
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Conditions
Conditions Yield
With oxygen; methylene blue; thiourea; In methanol; at 0 ℃; Yield given; Irradiation;
With oxygen; methylene blue; thiourea; In methanol; Irradiation;
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

(+/-)-(4α,5β)-4-hydroxy-5<(phenylmethoxy)methyl>-2-cyclopenten-1-one
100021-13-4

(+/-)-(4α,5β)-4-hydroxy-5<(phenylmethoxy)methyl>-2-cyclopenten-1-one

(1α,2α,3α)-2-<(phenylmethoxy)methyl>-4-cyclopentene-1,3-diol
100021-12-3

(1α,2α,3α)-2-<(phenylmethoxy)methyl>-4-cyclopentene-1,3-diol

Conditions
Conditions Yield
With oxygen; sodium acetate; rose bengal; thiourea; In methanol; at -5 ℃; for 9h; Yield given. Yields of byproduct given; Irradiation;
With oxygen; sodium acetate; rose bengal; thiourea; In methanol; at -5 ℃; for 9h; Yields of byproduct given; Irradiation;
thallium cyclopentadiene

thallium cyclopentadiene

Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

aqueous Na2 Cr2 O7

aqueous Na2 Cr2 O7

rose bengal
24545-87-7

rose bengal

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Conditions
Conditions Yield
With sodium acetate; thiourea; In methanol; ethyl acetate;
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

Conditions
Conditions Yield
With oxygen; methylene blue; thiourea; In methanol; at 0 ℃; Yield given; Irradiation;
With oxygen; methylene blue; thiourea; In methanol; Irradiation;
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

(+/-)-(4α,5β)-4-hydroxy-5<(phenylmethoxy)methyl>-2-cyclopenten-1-one
100021-13-4

(+/-)-(4α,5β)-4-hydroxy-5<(phenylmethoxy)methyl>-2-cyclopenten-1-one

(1α,2α,3α)-2-<(phenylmethoxy)methyl>-4-cyclopentene-1,3-diol
100021-12-3

(1α,2α,3α)-2-<(phenylmethoxy)methyl>-4-cyclopentene-1,3-diol

Conditions
Conditions Yield
With oxygen; sodium acetate; rose bengal; thiourea; In methanol; at -5 ℃; for 9h; Yield given. Yields of byproduct given; Irradiation;
With oxygen; sodium acetate; rose bengal; thiourea; In methanol; at -5 ℃; for 9h; Yields of byproduct given; Irradiation;

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