octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

Base Information

Chemical Name:octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside
CAS No.:950603-06-2
Molecular Formula:C₅₁H₅₈O₁₄
Molecular Weight:895.013
Hs Code.:

Synonyms:octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

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Technology Process of octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

There total 6 articles about octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside 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: 75.0%

: 950602-83-2
4-methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside

: 950603-04-0
octyl 4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

: 950603-06-2
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃;
DOI:10.1016/j.carres.2007.05.001

Reference yield:

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

: 950603-06-2
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / p-TsOH / acetone / 2 h

2: 84 percent / DMAP / acetonitrile

3: 88 percent / n-Bu₃SnH; AIBN / toluene / Heating

4: 72 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

5: 75 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 0 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; 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

: 950603-06-2
octyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / DMAP / acetonitrile

2: 88 percent / n-Bu₃SnH; AIBN / toluene / Heating

3: 72 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

4: 75 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 0 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.carres.2007.05.001