Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 123563-47-3
• Molecular Formula: C₂₂H₃₂O₁₂
• Molecular Weight: 488.489
• Mol file: 123563-47-3.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester 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: 69.8%

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(8-hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-ethoxy]-tetrahydro-pyran-4-yl ester (208645-03-8) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester (123563-47-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 18h;

DOI:10.1248/cpb.46.581

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester (123563-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / Zn / benzene / 1.5 h / 20 °C / Heating

2: 80 percent / LiAlH / diethyl ether / 2.8 h / 20 °C / Heating

3: 18 percent / Sulfolobus solfataricus crude homogenate / 75 °C

4: 163 mg / pyridine / 3 h / 20 °C

5: 110 mg / water; Dowex 50X₈-100 (H⁺ form) / 24 h / 20 °C

With pyridine; Dowex 50X₈-100 (H⁺ form); Sulfolobus solfataricus crude homogenate; water; zinc; In diethyl ether; benzene; 1: Reformatsky reaction / 2: Reduction / 3: transglucosidation / 4: Acetylation / 5: Hydrolysis;

DOI:10.1016/S0040-4020(97)00138-5

Reference yield:

(8-hydroxy-1,4-dioxaspiro[4,5]dec-8-yl)-acetic acid ethyl ester (189509-22-6) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexyl)-ethoxy]-tetrahydro-pyran-4-yl ester (123563-47-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / LiAlH / diethyl ether / 2.8 h / 20 °C / Heating

2: 18 percent / Sulfolobus solfataricus crude homogenate / 75 °C

3: 163 mg / pyridine / 3 h / 20 °C

4: 110 mg / water; Dowex 50X₈-100 (H⁺ form) / 24 h / 20 °C

With pyridine; Dowex 50X₈-100 (H⁺ form); Sulfolobus solfataricus crude homogenate; water; In diethyl ether; 1: Reduction / 2: transglucosidation / 3: Acetylation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(97)00138-5

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(8-hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-ethoxy]-tetrahydro-pyran-4-yl ester

cyclohexanedione monoethylene ketal

(8-hydroxy-1,4-dioxaspiro[4,5]dec-8-yl)-acetic acid ethyl ester

Downstream raw materials:

rengyoside B