methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside

Base Information

• Chemical Name: methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside
• CAS No.: 139212-86-5
• Molecular Formula: C₂₂H₂₉IO₃Si
• Molecular Weight: 496.46
• Mol file: 139212-86-5.mol

Synonyms:methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside

Chemical Property of methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside

There total 1 articles about methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside 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) + methyl iodide (74-88-4) → methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside (139212-86-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; Yield given. Multistep reaction; 1) toluene, -10 deg C, 0.5 h, 2) 80 deg C, 1.5 to 3 h;

DOI:10.1007/BF00808508

Reference yield: 70.0%

methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside (139212-86-5) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentafuranosyl)thymine (139212-87-6,139212-88-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -10 - 20 ℃;

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

Reference yield: 57.0%

methyl 5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside (139212-86-5) → disulfide of methyl 2,3-dideoxy-3-mercapto-5-O-(tert-butyldiphenylsilyl)-D-pentafuranoside

Guidance literature:

With sodium hydroxide; sulfur; In ethanol; at 78 ℃; for 1h;

DOI:10.1007/BF00808508

upstream raw materials:

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

methyl iodide

Downstream raw materials:

1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-α-D-threo-pentofuranosyl)-5-octyluracil

1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-β-D-threo-pentofuranosyl)-5-octyluracil

1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-α-D-threo-pentofuranosyl)-5-(methoxymethyl)uracil

1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-β-D-threo-pentofuranosyl)-5-(methoxymethyl)uracil