(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate
CAS No.:1467598-35-1
Molecular Formula:C₅₆H₆₆BrF₂NO₁₀
Molecular Weight:1031.04
Hs Code.:

(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

Synonyms:(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

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Chemical Property of (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

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Technology Process of (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

There total 13 articles about (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate 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: 69.0%

: 1308272-18-5
bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)methane

: (2S,3S,4R)-3,4-bis-O-benzyl-N-(tert-butoxycarbonyl)-2-amino-3,4-dihydroxynonanoic acid

: 1467598-35-1
(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

Guidance literature:: (2S,3S,4R)-3,4-bis-O-benzyl-N-(tert-butoxycarbonyl)-2-amino-3,4-dihydroxynonanoic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)methane; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/chem.201302070

Reference yield: 69.0%

: 1308272-18-5
bromo-difluoro-(3,4,6-tri-O-benzyl-α-D-galactopyranosyl)methane

: C₂₈H₃₉NO₆

: 1467598-35-1
(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

Guidance literature:: With dmap; diisopropyl-carbodiimide; Inert atmosphere;
DOI:10.1016/j.jfluchem.2015.02.014

Reference yield:

: 791611-26-2
(S)-4-((1S,2R)-1,2-Dihydroxy-heptyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 1467598-35-1
(2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(bromodifluoromethyl)tetrahydro-2H-pyran-3-yl (2R,3S,4R)-3,4-bis(benzyloxy)-2-((tertbutoxycarbonyl)amino)nonanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: acetic anhydride / water / 20 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Inert atmosphere; Reflux

4.1: sodium dihydrogen phosphate monohydrate; sodium chlorite / tert-butyl alcohol; water / 0 - 20 °C / Inert atmosphere

5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

With dmap; sodium chlorite; sodium dihydrogen phosphate monohydrate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; dicyclohexyl-carbodiimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.201302070