phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

Base Information

• Chemical Name: phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside
• CAS No.: 151929-70-3
• Molecular Formula: C₁₇H₂₂O₄S₂
• Molecular Weight: 354.491
• Mol file: 151929-70-3.mol

Synonyms:phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

Chemical Property of phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

There total 2 articles about phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside 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: 87.0%

phenylthiotrimethylsilane (4551-15-9) + methyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-2-thio-β-L-mannopyranoside (151929-69-0) → phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside (151929-70-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)73854-8

Reference yield:

methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside (151929-68-9) → phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside (151929-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine, 4-DMAP / 1.5 h / 25 °C

2: 87 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 25 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0040-4039(00)73854-8

Reference yield: 100.0%

diethyl(isopropyl)silyl trifluoromethanesulfonate (126889-55-2) + phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside (151929-70-3) → phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside (151929-61-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1016/S0040-4039(00)73854-8

upstream raw materials:

phenylthiotrimethylsilane

methyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-2-thio-β-L-mannopyranoside

methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside

Downstream raw materials:

phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

cyclohexyl 2,6-dideoxy-3-O-<2,6-dideoxy-3-O-(2,6-dideoxy-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-α-L-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl>-β-D-arabino-hexopyrnoside

cyclohexyl 2,6-anhydro-3-O-<2,6-anhydro-3-O-(2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-2-thio-β-L-mannopyranosyl)-4-O-benzyl-2-thio-β-D-mannosyl>-4-O-benzyl-2-thio-β-D-mannopyranoside