cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

Base Information

• Chemical Name: cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside
• CAS No.: 151957-70-9
• Molecular Formula: C₃₂H₄₀O₇S₂
• Molecular Weight: 600.797

Synonyms:cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

Chemical Property of cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

There total 11 articles about cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-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: 96.0%

cyclohexyl 3-O-(3-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-2,6-anhydro-4-O-benzyl-2-sulfinyl-β-D-mannopyranoside (151929-67-8) → cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside (151957-70-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

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

Reference yield: 79.0%

cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside (151957-71-0) → cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside (151957-70-9) + cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-mannopyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside (151957-72-1)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1021/ja00118a008

Reference yield:

1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (151929-60-1) → cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside (151957-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -30 - 0 °C

2: 96 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C

With lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00118a008

upstream raw materials:

cyclohexyl 3-O-(3-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-2,6-anhydro-4-O-benzyl-2-sulfinyl-β-D-mannopyranoside

cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

cyclohexyl 2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulose

1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose

Downstream raw materials:

cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulosyl)-4-O-benzyl-2-thio-β-D-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

cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-mannopyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside

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