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

Base Information

Chemical Name:1-methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octarate
CAS No.:578764-43-9
Molecular Formula:C₃₀H₃₂O₈
Molecular Weight:520.579
Hs Code.:

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

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Chemical Property of 1-methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octarate

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Technology Process of 1-methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octarate

There total 1 articles about 1-methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octarate 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: 87.0%

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

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

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
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

: (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 6 steps

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

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

3: 89 percent / EDC*HCl; HOBt; NMM / dimethylformamide / 16 h / 20 °C

4: TFA / CH₂Cl₂ / 0.08 h

5: 0.45 g / EDC*HCl; HOBt; NMM / dimethylformamide / 16 h / 0 °C

6: 100 percent / H₂ / Pd/C / methanol / 16 h

With 4-methyl-morpholine; sodium hydroxide; diphenyl phosphoryl azide; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: 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

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

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 89 percent / EDC*HCl; HOBt; NMM / dimethylformamide / 16 h / 20 °C

4: TFA / CH₂Cl₂ / 0.08 h

With 4-methyl-morpholine; sodium hydroxide; diphenyl phosphoryl azide; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Curtius rearrangement;
DOI:10.1002/ejoc.200210682