(2R,4R,5R)-2-(hydroxymethyl)-5-(4-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol

Base Information

• Chemical Name: (2R,4R,5R)-2-(hydroxymethyl)-5-(4-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol
• CAS No.: 16754-86-2
• Molecular Formula: C12H15 N3 O4 S
• Molecular Weight: 297.335
• Mol file: 16754-86-2.mol

Synonyms:NSC 105,826;NSC 105826;NSC-105,826;NSC-105826

Chemical Property of (2R,4R,5R)-2-(hydroxymethyl)-5-(4-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol

Chemical Property:

• Vapor Pressure: 5.51E-16mmHg at 25°C
• Boiling Point: 615.1°Cat760mmHg
• Flash Point: 325.8°C
• PSA: 125.93000
• Density: 1.72g/cm³
• LogP: -0.23530
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 297.07832714
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=NC=NC2=C1C=CN2C3C(C(C(O3)CO)O)O
• Isomeric SMILES: CSC1=NC=NC2=C1C=CN2[C@H]3[C@@H](C([C@H](O3)CO)O)O

Technology Process of (2R,4R,5R)-2-(hydroxymethyl)-5-(4-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol

There total 6 articles about (2R,4R,5R)-2-(hydroxymethyl)-5-(4-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-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: 68.0%

7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine (120401-29-8) → 4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (16754-86-2)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1002/hlca.19880710623

Reference yield: 46.0%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate (29914-75-8) + sodium thiomethoxide (5188-07-8) → 4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (16754-86-2)

Guidance literature:

In ethanol; at 20 ℃; for 4h;

DOI:10.1021/jm4018948

Reference yield:

2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride (102690-94-8) → 4-(methylthio)-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine (16754-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran

2: 68 percent / 10percent aq.CF₃COOH

With potassium hydroxide; trifluoroacetic acid; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran;

DOI:10.1002/hlca.19880710623

upstream raw materials:

7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-4-(methylthio)-7H-pyrrolo<2,3-d>pyrimidine

2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate

Downstream raw materials:

tubercidin