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

Base Information

Chemical Name: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
CAS No.:151957-73-2
Molecular Formula:C₅₀H₇₂O₁₁S₃Si
Molecular Weight:973.399
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 17 articles about 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 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: 89.0%

: 151929-61-2
phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside

: 151957-72-1
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

: 151957-73-2
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

Guidance literature:: With N-Bromosuccinimide; MS 4 Angstroem; In dichloromethane; at -30 - -20 ℃; for 0.666667h;
DOI:10.1016/S0040-4039(00)73854-8

Reference yield:

: 151929-60-1
1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose

: 151957-73-2
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

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

4: 79 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C

5: 89 percent / 4A molecular sieves, N-bromosuccinimide / CH₂Cl₂ / 0.5 h / -30 - -20 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00118a008

Reference yield:

: (1S,3S,4S,7R,8R)-7-Benzyloxy-3-methoxy-8-(tetrahydro-pyran-2-yloxy)-2-oxa-5-thia-bicyclo[2.2.2]octane

: 151957-73-2
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

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / TMSOTf / 1 h / 0 °C

2: 89 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -30 - 0 °C

3: 96 percent / lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C

4: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

5: 79 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C

6: 89 percent / 4A molecular sieves, N-bromosuccinimide / CH₂Cl₂ / 0.5 h / -30 - -20 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00118a008