Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester

Base Information

• Chemical Name: Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester
• CAS No.: 104112-08-5
• Molecular Formula: C₃₆H₄₈O₁₄
• Molecular Weight: 704.769
• Mol file: 104112-08-5.mol

Synonyms:

Chemical Property of Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester

There total 2 articles about Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl 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:

Acetic acid (1R,6R)-2,2,6-trimethyl-1-((E)-3-oxo-but-1-enyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (104056-86-2) → Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester (104112-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 mg / NaBH₄ / methanol / 0.5 h / 28 °C

2: 2 mg / pyridine / 8 h / 30 °C

With pyridine; sodium tetrahydroborate; In methanol;

DOI:10.1248/cpb.44.41

Reference yield:

benzoyl chloride (98-88-4) + Acetic acid (1R,6R)-1-((E)-(R)-3-hydroxy-but-1-enyl)-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (104112-07-4) → Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester (104112-08-5)

Guidance literature:

With pyridine;

DOI:10.1248/cpb.34.2294

Reference yield:

Benzoic acid (E)-(R)-3-[(1R,6R)-1-acetoxy-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-1-methyl-allyl ester (104112-08-5) → rehmaionoside B (104056-83-9)

Guidance literature:

With sodium methylate; In methanol; Product distribution;

DOI:10.1248/cpb.34.2294

upstream raw materials:

benzoyl chloride

Acetic acid (1R,6R)-1-((E)-(R)-3-hydroxy-but-1-enyl)-2,2,6-trimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

Acetic acid (1R,6R)-2,2,6-trimethyl-1-((E)-3-oxo-but-1-enyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

Downstream raw materials:

rehmaionoside B