methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

Base Information

Chemical Name:methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate
CAS No.:134258-03-0
Molecular Formula:C₄₀H₄₅NO₉
Molecular Weight:683.799
Hs Code.:

Synonyms:methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

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Chemical Property of methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

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Technology Process of methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

There total 4 articles about methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate 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: 91.0%

: 134258-02-9
methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-bromo-2,5-dideoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

: 134258-03-0
methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 60 ℃; for 0.5h;
DOI:10.1002/hlca.19910740223

Reference yield:

: 116096-63-0
methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

: 134258-03-0
methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / NBS / acetonitrile; H₂O / 0.33 h / 70 °C

2: 85 percent / DBU / acetonitrile / 0.17 h / Ambient temperature

3: 61 percent / TiBr₄ / 1,2-dichloro-ethane / 0.08 h / -40 °C

4: 91 percent / Bu₃SnH, AIBN / benzene / 0.5 h / 60 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; titanium(IV) bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; 1,2-dichloro-ethane; acetonitrile; benzene;
DOI:10.1002/hlca.19910740223

Reference yield:

: 134258-01-8
methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

: 134258-03-0
methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

Guidance literature:: Multi-step reaction with 2 steps

1: 61 percent / TiBr₄ / 1,2-dichloro-ethane / 0.08 h / -40 °C

2: 91 percent / Bu₃SnH, AIBN / benzene / 0.5 h / 60 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; titanium(IV) bromide; In 1,2-dichloro-ethane; benzene;
DOI:10.1002/hlca.19910740223