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

Base Information

Chemical Name:methyl 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonate
CAS No.:578764-44-0
Molecular Formula:C₃₄H₄₁NO₈
Molecular Weight:591.701
Hs Code.:

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

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

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

There total 1 articles about methyl 3,7-anhydro-4,5,6-tri-O-benzyl-7-(tert-butoxycarbonylamino)-2-deoxy-D-gulo-D-glycero-heptonate 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:

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

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

Guidance literature:: Multi-step reaction with 2 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

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

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:

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

: (S)-2-[(S)-2-(2-{(2S,3R,4R,5S,6S)-6-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3,4,5-trihydroxy-tetrahydro-pyran-2-yl}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / NaOH; water / dioxane / 3 h

2: 89 percent / EDC*HCl; HOBt; NMM / dimethylformamide / 16 h / 20 °C

3: TFA / CH₂Cl₂ / 0.08 h

4: 0.45 g / EDC*HCl; HOBt; NMM / dimethylformamide / 16 h / 0 °C

5: 100 percent / H₂ / Pd/C / methanol / 16 h

With 4-methyl-morpholine; sodium hydroxide; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200210682