Welcome to LookChem.com Sign In|Join Free

Cas Database

100101-49-3

100101-49-3

Identification

  • Product Name:(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

  • CAS Number: 100101-49-3

  • EINECS:

  • Molecular Weight:531.609

  • Molecular Formula: C30H33N3O6

  • HS Code:

  • Mol File:100101-49-3.mol

Synonyms:

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 1 Articles be found

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

5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: O2, thiourea, sodium acetate, Rose bengal / methanol / 9 h / -5 °C / Irradiation
2: 62 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature
3: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
4: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
5: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
(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

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 62 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature
2: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
3: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
4: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: oxalyl chloride / benzene; dimethylformamide / 1 h / Ambient temperature
2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; benzene;
2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
100021-14-5

2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
2: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
3: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; In dichloromethane; N,N-dimethyl-formamide; acetone;
(+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol
100021-15-6

(+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; perchloric acid; In dichloromethane; acetone;
(S)-naproxenoyl chloride
51091-84-0

(S)-naproxenoyl chloride

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100021-16-7

(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

<1S-(1β,2α,3α,4β,5α)>-2,3-(dimethylmethylenedioxy)-5-<(S)-(2-(6-methoxy-2-naphthyl)propionyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide
100021-25-8

<1S-(1β,2α,3α,4β,5α)>-2,3-(dimethylmethylenedioxy)-5-<(S)-(2-(6-methoxy-2-naphthyl)propionyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
With pyridine; dmap; In dichloromethane; for 2h; Yield given. Yields of byproduct given; Ambient temperature;
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: O2, thiourea, sodium acetate, Rose bengal / methanol / 9 h / -5 °C / Irradiation
2: 62 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature
3: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
4: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
5: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
(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

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 62 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature
2: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
3: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
4: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: oxalyl chloride / benzene; dimethylformamide / 1 h / Ambient temperature
2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; benzene;
2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
100021-14-5

2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
100101-49-3

(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
2: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
3: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
With pyridine; dmap; sodium azide; perchloric acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

Global suppliers and manufacturers

Global( 0) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 100101-49-3
Post Buying Request Now
close
Remarks: The blank with*must be completed