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

Base Information

Chemical Name: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
CAS No.:151929-67-8
Molecular Formula:C₃₄H₄₂O₉S₂
Molecular Weight:658.834
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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%

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

: 151957-69-6
cyclohexyl 2,6-anhydro-4-O-benzyl-2-sulfinyl-β-D-mannopyranoside

: 151929-67-8
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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 0 ℃; for 1.5h;
DOI:10.1016/S0040-4039(00)73854-8

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

: 151929-67-8
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

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / TMSOTf / 1 h / 0 °C

2: 90 percent / TMSOTf / CH₂Cl₂ / 0.33 h / -40 - -20 °C

3: 99 percent / NaOMe / methanol / 1 h / 25 °C

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

5: 86 percent / diisobutylaluminum hydride / toluene / 1.25 h / -78 °C

6: 100 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.25 h / 0 °C

7: 89 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -30 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; diisobutylaluminium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; toluene;
DOI:10.1021/ja00118a008

Reference yield:

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

: 151929-67-8
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

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / TMSOTf / CH₂Cl₂ / 0.33 h / -40 - -20 °C

2: 99 percent / NaOMe / methanol / 1 h / 25 °C

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

4: 86 percent / diisobutylaluminum hydride / toluene / 1.25 h / -78 °C

5: 100 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.25 h / 0 °C

6: 89 percent / TMSOTf / CH₂Cl₂ / 1.5 h / -30 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; diisobutylaluminium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; toluene;
DOI:10.1021/ja00118a008