methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

Base Information

Chemical Name:methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate
CAS No.:441778-40-1
Molecular Formula:C₃₄H₄₁NO₈
Molecular Weight:591.701
Hs Code.:

Synonyms:methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

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

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

There total 6 articles about methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate 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: 64.0%

: 124-41-4
sodium methylate

: 100-39-0
benzyl bromide

: 441778-39-8
methyl 2,6-anhydro-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

: 441778-40-1
methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: benzyl bromide; methyl 2,6-anhydro-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

sodium methylate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: 185114-94-7,155417-78-0
1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

: 441778-40-1
methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 62 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 36 h / 20 °C

2.1: 57 percent / nitromethane / 1 h / 80 °C

3.1: NaOMe / methanol / 1 h / 20 °C / pH 11

3.2: NaOH / H₂O / 12 h / Heating

4.1: 1.30 g / 12 h / Heating

5.1: H₂S / pyridine; H₂O / 14 h / 20 °C

6.1: 1.02 g / Et₃N / methanol / 12 h / 20 °C

7.1: NaH / dimethylformamide / 12 h / 20 °C

7.2: 64 percent / methanol / 2 h / 20 °C

With hydrogen sulfide; sodium methylate; titanium(IV) bromide; sodium hydride; triethylamine; In pyridine; methanol; nitromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: (2R,3R,4S,5S,6R)-4-Amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester

: 441778-40-1
methyl 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1.02 g / Et₃N / methanol / 12 h / 20 °C

2.1: NaH / dimethylformamide / 12 h / 20 °C

2.2: 64 percent / methanol / 2 h / 20 °C

With sodium hydride; triethylamine; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2