(1R,2S,3S,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Base Information

• Chemical Name: (1R,2S,3S,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS No.: 72346-00-0
• Molecular Formula: C₁₁H₁₅N₅O₃
• Molecular Weight: 265.272
• Mol file: 72346-00-0.mol

Synonyms:

Chemical Property of (1R,2S,3S,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Chemical Property:

• Vapor Pressure: 5.19E-15mmHg at 25°C
• Boiling Point: 595.1°Cat760mmHg
• Flash Point: 313.7°C
• Density: 1.92g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S,3S,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

There total 19 articles about (1R,2S,3S,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol 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: 55.0%

(+/-)-cis-9H-9-<4-(hydroxymethyl)-2-cyclopenten-1-yl>adenine (118237-82-4,121481-93-4,147332-45-4) → (+/-)-C-Adenosine (13190-75-5) + (+/-)-9-<2α,3α-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>adenine (72346-00-0)

Guidance literature:

With osmium(VIII) oxide; In N,N-dimethyl-formamide; at -15 ℃; for 36h;

DOI:10.1021/jo9919759

Reference yield:

6-oxabicyclo<3.1.0>hex-2-ene (7129-41-1,54460-11-6) → (+/-)-9-<2α,3α-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>adenine (72346-00-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 67 percent / <(i-C₃H₇O)3P>4Pd / tetrahydrofuran; dimethylsulfoxide / 1.) 0 deg C for 3 h 2.) 25 deg C overnight

2: 85 percent / piridine / CH₂Cl₂ / from 0 deg C to room temperature

3: 82 percent / Ph₃P / (dba)3Pd₂(CHCl₃) / tetrahydrofuran / Heating

4: osmium tetroxide, N-methyl-morpholine N-oxide / tetrahydrofuran; H₂O

5: TsOH / acetone / 50 °C

6: NH₄OH / methanol / Ambient temperature

7: NaOCH₃, O₃ / -78 °C

8: DIBAL-H / CH₂Cl₂; benzene / 45 °C

9: 1.5 M aq. HCl / 80 °C

With pyridine; hydrogenchloride; ammonium hydroxide; osmium(VIII) oxide; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; C₃₆H₈₄O₁₂P₄Pd; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetone; benzene;

DOI:10.1021/ja00210a064

Reference yield:

(1R,4S)-4-(6-Amino-purin-9-yl)-cyclopent-2-enol (111189-91-4) → (+/-)-9-<2α,3α-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>adenine (72346-00-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / piridine / CH₂Cl₂ / from 0 deg C to room temperature

2: 82 percent / Ph₃P / (dba)3Pd₂(CHCl₃) / tetrahydrofuran / Heating

3: osmium tetroxide, N-methyl-morpholine N-oxide / tetrahydrofuran; H₂O

4: TsOH / acetone / 50 °C

5: NH₄OH / methanol / Ambient temperature

6: NaOCH₃, O₃ / -78 °C

7: DIBAL-H / CH₂Cl₂; benzene / 45 °C

8: 1.5 M aq. HCl / 80 °C

With pyridine; hydrogenchloride; ammonium hydroxide; osmium(VIII) oxide; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;

DOI:10.1021/ja00210a064

upstream raw materials:

diethoxymethyl acetate

(+/-)-5-amino-4-<<2α,3α-dihydroxy-4α-(hydroxymethyl)-cyclopent-1α-yl>amino>-6-chloropyrimidine

[(3aR,4S,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-methanol

(+/-)-cis-9H-9-<4-(hydroxymethyl)-2-cyclopenten-1-yl>adenine