1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-methoxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (non-preferred name)

Base Information

• Chemical Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-methoxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (non-preferred name)
• CAS No.: 140360-37-8
• Molecular Formula: C₁₁H₁₆N₂O₆
• Molecular Weight: 272.258
• Mol file: 140360-37-8.mol

Synonyms:

Chemical Property of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-methoxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (non-preferred name)

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.48g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-methoxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (non-preferred name)

There total 8 articles about 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-5-methoxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (non-preferred name) 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: 92.0%

3'-O-tert-butyldiphenylsilyl-4'-methoxythymidine → 4'-methoxythymidine (140226-29-5,140360-37-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acs.orglett.5b01430

Reference yield: 34.0%

methanol (67-56-1) + 1-((2R,4S)-4-hydroxy-5-methylenetetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (28034-72-2) → 4'-methoxythymidine (140226-29-5,140360-37-8) + 1-(2-deoxy-4-methoxy-α-L-threo-pentofuranosyl)thymine (140226-29-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; for 4h; Ambient temperature;

Reference yield:

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (25953-14-4,94892-66-7) → 4'-methoxythymidine (140226-29-5,140360-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / sodium methoxide / methanol / 16 h / Heating

2: 19 percent / m-chloroperbenzoic acid / 1 h

With sodium methylate; 3-chloro-benzenecarboperoxoic acid; In methanol;

DOI:10.1021/jm00086a013

upstream raw materials:

methanol

1-((2R,4S)-4-hydroxy-5-methylenetetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

thymidine