(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

Base Information

Chemical Name:(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate
CAS No.:768385-15-5
Molecular Formula:C₄₄H₄₈NO₉P
Molecular Weight:765.84
Hs Code.:

Synonyms:(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

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Chemical Property of (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

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Technology Process of (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

There total 3 articles about (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate 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: 94.0%

: 17176-77-1
Dibenzyl phosphite

: 260551-11-9
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-1-hydroxy-D-glycero-D-ido-heptitol

: 768385-15-5
(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

Guidance literature:: 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-1-hydroxy-D-glycero-D-ido-heptitol; With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

Dibenzyl phosphite; With triethylamine; at 20 ℃; for 2h;
DOI:10.1002/ejoc.200400197

Reference yield:

: 260551-08-4
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptonic acid

: 768385-15-5
(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: carbonyldiimidazole / dimethylformamide / 2.5 h / 0 - 20 °C

1.2: 93 percent / dimethylformamide / 1.5 h / 20 °C

2.1: 93 percent / sodium borohydride / CH₂Cl₂; ethanol / 3 h / 0 - 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.2: 94 percent / triethylamine / 2 h / 20 °C

With sodium tetrahydroborate; Dess-Martin periodane; 1,1'-carbonyldiimidazole; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400197

Reference yield:

: (2S,3S,4R,5S,6R)-3-Amino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonitrile

: 768385-15-5
(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.5 g / pyridine / 48 h / 20 °C

2.1: 50 percent / HCl / dioxane; H₂O / 20 h / 60 °C

3.1: carbonyldiimidazole / dimethylformamide / 2.5 h / 0 - 20 °C

3.2: 93 percent / dimethylformamide / 1.5 h / 20 °C

4.1: 93 percent / sodium borohydride / CH₂Cl₂; ethanol / 3 h / 0 - 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.2: 94 percent / triethylamine / 2 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; Dess-Martin periodane; 1,1'-carbonyldiimidazole; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400197