Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester
CAS No.:134760-60-4
Molecular Formula:C₂₁H₂₃N₅O₁₀S₂
Molecular Weight:569.573
Hs Code.:

Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

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Chemical Property of Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

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Technology Process of Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

There total 6 articles about Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester 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: 40.0%

: 134760-76-2
2-Amino-9-(3-O-mesyl-5-O-(methoxycarbonyl)-β-D-xylofuranosyl)-6-methoxy-9H-purine

: 1005-56-7
phenylcarbonochloridothioate

: 134760-60-4
Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: With dmap; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)93545-7

Reference yield:

: 5432-33-7
3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside

: 134760-60-4
Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / NEt₃ / CH₂Cl₂ / 1) rt, 1.5 h, 2) 4 deg C, 16 h

2: 76 percent / conc. H₂SO₄, glacial acetic acid / 16 h / Ambient temperature

3: 1) N,O-bis(trimethylsilyl)acetamide, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, 80 deg C, 2) toluene, 80 deg C, 2 h, then rt, overnight

4: 80 percent / acetyl chloride / 18 h / Ambient temperature

5: 40 percent / DMAP / acetonitrile; CH₂Cl₂

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; triethylamine; acetyl chloride; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)93545-7

Reference yield:

: 74595-09-8
1,2-O-isopropylidene-3-O-mesyl-5-O-(methoxycarbonyl)-α-D-xylofuranose

: 134760-60-4
Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / conc. H₂SO₄, glacial acetic acid / 16 h / Ambient temperature

2: 1) N,O-bis(trimethylsilyl)acetamide, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, 80 deg C, 2) toluene, 80 deg C, 2 h, then rt, overnight

3: 80 percent / acetyl chloride / 18 h / Ambient temperature

4: 40 percent / DMAP / acetonitrile; CH₂Cl₂

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; acetyl chloride; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)93545-7