methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

Base Information

Chemical Name:methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate
CAS No.:321549-91-1
Molecular Formula:C₂₇H₃₁NO₁₆
Molecular Weight:625.54
Hs Code.:

Synonyms:methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

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Chemical Property of methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

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Technology Process of methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

There total 3 articles about methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate 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%

: methyl {5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylidene]-D-glycero-β-D-talo-oct-2-ulopyranos}onate

: 321549-91-1
methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1016/S0008-6215(00)00213-5

Reference yield:

: 321549-86-4
methyl [3,5,7,8-tetra-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosyl bromide]onate

: 321549-91-1
methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / Hg(CN)2; 4 Angstroem molecular sieves / CHCl₃ / 2 h / 40 °C

2: 74 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; mercury(II) cyanide; In dichloromethane; chloroform; 1: Helferich conditions;
DOI:10.1016/S0008-6215(00)00213-5

Reference yield:

: 321549-84-2
methyl [3,5,7,8-tetra-O-acetyl-2,4-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate

: 321549-91-1
methyl [allyl 5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranosid]onate

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / TiBr₄ / CH₂Cl₂ / 12 h / Heating

2: 95 percent / Hg(CN)2; 4 Angstroem molecular sieves / CHCl₃ / 2 h / 40 °C

3: 74 percent / trimethylsilyl trifluoromethanesulfonate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; mercury(II) cyanide; titanium(IV) bromide; In dichloromethane; chloroform; 2: Helferich conditions;
DOI:10.1016/S0008-6215(00)00213-5