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

Base Information

Chemical Name:2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic acid
CAS No.:264616-06-0
Molecular Formula:C₃₃H₃₉NO₈
Molecular Weight:577.675
Hs Code.:

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

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

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

There total 6 articles about 2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic 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: 97.0%

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

: 264616-06-0
2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.333333h;
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

: 264616-06-0
2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic acid

Guidance literature:: Multi-step reaction with 8 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

8.1: 97 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 20 °C

With lithium hydroxide; hydrogen sulfide; sodium methylate; titanium(IV) bromide; sodium hydride; triethylamine; In tetrahydrofuran; 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

: 264616-06-0
2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic acid

Guidance literature:: Multi-step reaction with 3 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

3.1: 97 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 20 °C

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