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

Base Information

Chemical Name:methyl 2,6-anhydro-5-azido-3,4,7-tri-O-benzyl-5-deoxy-D-glycero-D-gulo-hepturonate
CAS No.:441778-47-8
Molecular Formula:C₂₉H₃₁N₃O₆
Molecular Weight:517.582
Hs Code.:

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

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

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

There total 8 articles about methyl 2,6-anhydro-5-azido-3,4,7-tri-O-benzyl-5-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:

: (2R,3R,4R,5S,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 441778-47-8
methyl 2,6-anhydro-5-azido-3,4,7-tri-O-benzyl-5-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)01764-4

Reference yield:

: 57039-37-9
(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate

: 441778-47-8
methyl 2,6-anhydro-5-azido-3,4,7-tri-O-benzyl-5-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 61 percent / HCO₂H / 1 h / 20 °C

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

2.2: 93 percent / methanol / 2 h / 20 °C / pH 11

3.1: 94 percent / HCl; NaBH₃CN; 3 Angstroem molecular sieves / ethyl acetate; tetrahydrofuran / 0.33 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 2 h / -15 °C

5.1: 1.20 g / NaN₃ / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; formic acid; sodium azide; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: 197720-07-3
methyl 2,6-anhydro-3,4,7-tri-O-benzyl-D-glycero-L-manno-hepturonate

: 441778-47-8
methyl 2,6-anhydro-5-azido-3,4,7-tri-O-benzyl-5-deoxy-D-glycero-D-gulo-hepturonate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 2 h / -15 °C

2: 1.20 g / NaN₃ / dimethylformamide / 12 h / 20 °C

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2