3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

Base Information

Chemical Name:3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid
CAS No.:578764-45-1
Molecular Formula:C₃₃H₃₉NO₈
Molecular Weight:577.675
Hs Code.:

Synonyms:3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

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Chemical Property of 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

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Technology Process of 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

There total 3 articles about 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid 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: 80.0%

: 578764-44-0
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonate

: 578764-45-1
3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

Guidance literature:: With sodium hydroxide; water; In 1,4-dioxane; for 3h;
DOI:10.1002/ejoc.200210682

Reference yield:

: 578764-42-8
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octulonate

: 578764-45-1
3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / 4A MS; pyridinium dichromate / dimethylformamide / 16 h / 20 °C

2: 75 percent / 4A MS; diphenylphosphorazide; Et₃N / toluene / 16 h / 80 °C

3: 80 percent / NaOH; water / dioxane / 3 h

With sodium hydroxide; dipyridinium dichromate; diphenyl phosphoryl azide; water; triethylamine; In 1,4-dioxane; N,N-dimethyl-formamide; toluene; 2: Curtius rearrangement;
DOI:10.1002/ejoc.200210682

Reference yield:

: 578764-43-9
1-methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octarate

: 578764-45-1
3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / 4A MS; diphenylphosphorazide; Et₃N / toluene / 16 h / 80 °C

2: 80 percent / NaOH; water / dioxane / 3 h

With sodium hydroxide; diphenyl phosphoryl azide; water; triethylamine; In 1,4-dioxane; toluene; 1: Curtius rearrangement;
DOI:10.1002/ejoc.200210682