octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

Base Information

Chemical Name:octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside
CAS No.:950602-88-7
Molecular Formula:C₆₉H₆₈O₁₇S
Molecular Weight:1201.35
Hs Code.:

Synonyms:octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

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Chemical Property of octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

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Technology Process of octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

There total 9 articles about octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-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: 74.0%

: 950602-86-5
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-α-D-mannopyranoside

: 1005-56-7
phenylcarbonochloridothioate

: 950602-88-7
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

Guidance literature:: With dmap; In acetonitrile;
DOI:10.1016/j.carres.2007.05.001

Reference yield:

: 950602-63-8
octyl 6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside

: 950602-88-7
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / p-TsOH / acetone / 2 h

2.1: NaH / dimethylformamide / 20 °C

3.1: 1.29 g / n-Bu₄NF / tetrahydrofuran / 20 °C

4.1: 92 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 0 °C

5.1: 88 percent / aq. AcOH / 50 °C

6.1: Bu₂SnO / toluene / 3 h / 110 °C

6.2: 63 percent / toluene / 20 °C

7.1: 74 percent / DMAP / acetonitrile

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/j.carres.2007.05.001

Reference yield:

: 950602-81-0
octyl 2,3-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside

: 950602-88-7
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-benzoyl-4-O-benzyl-2-O-phenoxythiocarbonyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 20 °C

2.1: 1.29 g / n-Bu₄NF / tetrahydrofuran / 20 °C

3.1: 92 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 0 °C

4.1: 88 percent / aq. AcOH / 50 °C

5.1: Bu₂SnO / toluene / 3 h / 110 °C

5.2: 63 percent / toluene / 20 °C

6.1: 74 percent / DMAP / acetonitrile

With dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.carres.2007.05.001