Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 139212-94-5
• Molecular Formula: C₂₇H₃₄N₂O₇SSi
• Molecular Weight: 558.728
• Mol file: 139212-94-5.mol

Synonyms:

Chemical Property of Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 2 articles about Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-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:

methyl-5-O-tert-butyldiphenylsilyl-2-deoxy-ribo-furanoside (127306-47-2) → Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (139212-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 2 h / 0 °C

2: TMS-triflate / acetonitrile / 4 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In pyridine; acetonitrile;

DOI:10.3891/acta.chem.scand.45-1060

Reference yield:

methyl 5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-methylsulfonyl-D-erythro-pentofuranoside (139212-93-4) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → Methanesulfonic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (139212-94-5) + 5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine (139212-95-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 4h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.3891/acta.chem.scand.45-1060

Reference yield: 35.0%

1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methylsulfonyl-α,β-D-erythro-pentofuranosyl)thymine (139212-94-5,139212-95-6) → 1-(3,5-anhydro-2-deoxy-α-D-threo-pentofuranosyl)thymine + 1-(2,3-dideoxy-D-glycero-pent-2-enofuranosyl)thymine (3056-17-5,26638-87-9,84414-90-4,133008-05-6,135212-56-5) + threothymidine (16053-52-4,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With sodium methylate; In methanol; for 24h; Heating;

DOI:10.3891/acta.chem.scand.45-1060

upstream raw materials:

methyl 5-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-methylsulfonyl-D-erythro-pentofuranoside

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

methyl-5-O-tert-butyldiphenylsilyl-2-deoxy-ribo-furanoside

Downstream raw materials:

1-(2,3-dideoxy-D-glycero-pent-2-enofuranosyl)thymine

threothymidine

2,3'-anhydrothymidine

stavudin