allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

Base Information

Chemical Name:allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside
CAS No.:1262326-51-1
Molecular Formula:C₃₁H₃₃BrO₅
Molecular Weight:565.504
Hs Code.:

Synonyms:allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

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Chemical Property of allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

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Technology Process of allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

There total 5 articles about allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside 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: 14.0%

: 107-18-6
allyl alcohol

: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1,2-C-(dibromomethylene)-D-glycero-D-gulo-hexitol

: (Z)-1-O-allyl-3,6-anhydro-4,5,7-tri-O-benzyl-2-bromo-2-deoxy-D-arabino-hept-1-enitol

: 1262326-52-2
allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-α-D-arabino-hept-2-enoseptanoside

: 1262326-51-1
allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

: 3,6-anhydro-4,5,7-tri-O-benzyl-2-bromo-2-deoxy-D-arabino-septanose diallyl acetal

Guidance literature:: With silver trifluoroacetate; at 98 ℃; for 72h; optical yield given as %de; Inert atmosphere;
DOI:10.1039/c0cc02244f

Reference yield:

: 13265-84-4
D-glucal

: 1262326-51-1
allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.42 h / 0 °C / Inert atmosphere

1.2: 17 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydroxide; potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride / water / 72 h / 20 °C / Inert atmosphere

3.1: 25 h / Inert atmosphere; Darkness; Reflux

With potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride; sodium hydride; sodium hydroxide; In water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2014.06.069

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 1262326-51-1
allyl 4,5,7-tri-O-benzyl-2-bromo-2,3-dideoxy-β-D-arabino-hept-2-enoseptanoside

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydroxide; potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride / water / 72 h / 20 °C / Inert atmosphere

2: 25 h / Inert atmosphere; Darkness; Reflux

With potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In water;
DOI:10.1016/j.tet.2014.06.069