phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

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Chemical Name:phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside
CAS No.:148853-10-5
Molecular Formula:C₅₂H₆₀O₇S₃Si₂
Molecular Weight:949.413
Hs Code.:

phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

Synonyms:phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

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Chemical Property of phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

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Technology Process of phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

There total 4 articles about phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-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: 90.0%

: 108-24-7
acetic anhydride

: 148853-09-2
phenyl 2,6-anhydro-4-O-(2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

: 148853-10-5
phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

Guidance literature:: With pyridine; dmap;
DOI:10.1016/0040-4039(93)85021-N

Reference yield:

: 148853-08-1
phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-sulfinyl-1-thio-α-D-mannopyranoside

: 148853-10-5
phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / LiAlH₄ / tetrahydrofuran / 1 h

2: 90 percent / 4-DMAP, pyridine / 0.5 h

With pyridine; dmap; lithium aluminium tetrahydride; In tetrahydrofuran;
DOI:10.1021/ja00099a022

Reference yield:

: Acetic acid (1S,4S,7R,8S)-8-(tert-butyl-diphenyl-silanyloxy)-3-phenylsulfanyl-2-oxa-5-thia-bicyclo[2.2.2]oct-7-yl ester

: 148853-10-5
phenyl 4-O-(4-O-acetyl-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-2-thio-α-D-mannopyranosyl)-2,6-anhydro-3-O-(tert-butyldiphenylsilyl)-1,2-dithio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / NIS, TMSOTf / CH₂Cl₂ / 0.25 h / -40 °C

2: 86 percent / LiAlH₄ / tetrahydrofuran / 1 h

3: 90 percent / 4-DMAP, pyridine / 0.5 h

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00099a022