(1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate

Base Information

• Chemical Name: (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate
• CAS No.: 42442-75-1
• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.371

Synonyms:(1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate

Chemical Property of (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate

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Technology Process of (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate

There total 9 articles about (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate 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: 93.0%

acetic anhydride (108-24-7) + pinitol (10284-63-6) → (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate (42442-75-1)

Guidance literature:

With pyridine; dmap; at 20 ℃;

Reference yield: 26.0%

(1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol (6090-97-7) + acetic anhydride (108-24-7) → (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate (42442-75-1)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 16h;

Reference yield:

(1R)-O1,O5,O6-triacetyl-O4-methyl-2,3-anhydro-allo-inositol (18391-50-9) → (1R,2R,3R,4S,5R,6R)-2,3,4,6-tetrakis(acetyloxy)-5-methoxycyclohexyl acetate (42442-75-1) + penta-O-acetyl-1-O-methyl-muco-inositol (17230-39-6,18391-40-7,18391-41-8,20254-33-5,42442-75-1,51546-78-2,54324-59-3,64314-41-6,64314-42-7,74560-61-5,94482-10-7,98461-53-1,98461-54-2,98461-55-3,98461-56-4,98461-57-5,116497-06-4,134235-51-1,135267-03-7)

Guidance literature:

With sulfuric acid; Erwaermen des Reaktionsprodukts mit Acetanhydrid und Natriumacetat;

DOI:10.1021/ja01621a047

upstream raw materials:

acetic anhydride

pinitol

(1R)-O¹,O⁵,O⁶-triacetyl-O⁴-methyl-2,3-anhydro-allo-inositol

(1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

Downstream raw materials:

D-1,2,4,5-tetra-O-acetyl-3-O-methyl-chiro-inositol

D-1,2,3,5-tetra-O-acetyl-4-O-methyl-chiro-inositol

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