(2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose

Base Information

• Chemical Name: (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose
• CAS No.: 455886-05-2
• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.43

Synonyms:(2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose

Chemical Property of (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose

Chemical Property:

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Technology Process of (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose

There total 3 articles about (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose 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: 90.0%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) + acetic anhydride (108-24-7) → (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose (455886-05-2)

Guidance literature:

3,4,6-tri-O-benzyl-D-galactal; With sulfuric acid; mercury(II) sulfate; In 1,4-dioxane; at 20 ℃; for 8h;

acetic anhydride; With pyridine; at 5 ℃;

DOI:10.1016/j.carres.2004.05.027

Reference yield: 45.0%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) + acetic anhydride (108-24-7) → (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose (455886-05-2) + (3S,4S,5R)-3,4,6-tri-O-benzyl-2-deoxy-D-lyxo-hexopyranose acetate

Guidance literature:

3,4,6-tri-O-benzyl-D-galactal; With sulfuric acid; mercury(II) sulfate; In tetrahydrofuran; at 75 ℃; for 3h;

acetic anhydride; With pyridine; at 5 ℃;

DOI:10.1016/j.carres.2004.05.027

Reference yield:

acetic anhydride (108-24-7) + (2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-threo-hex-2-enose (137410-20-9) → (2E,4R,5R)-5-O-acetyl-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-erythro-hex-enose (455886-05-2)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1021/ol802915h

upstream raw materials:

3,4,6-tri-O-benzyl-D-galactal

acetic anhydride

(2E)-4,6-di-O-benzyl-2,3-dideoxy-aldehydo-D-threo-hex-2-enose

Downstream raw materials:

(2R,3R,4E,6E)-1,3-bis(benzyloxy)octadeca-4,6-dien-2-yl acetate

(2R,3R)-1,3-bis(benzyloxy)-6-oxohexan-2-yl acetate

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