1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol

Base Information

• Chemical Name: 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol
• CAS No.: 769931-80-8
• Molecular Formula: C₂₆H₃₄O₈
• Molecular Weight: 474.551
• Mol file: 769931-80-8.mol

Synonyms:1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol

Chemical Property of 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol

There total 3 articles about 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 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: 89.0%

(1R,2R,3S,4S,5S,6R)-5-(4-pivaloyloxy)-6-hydroxy-(1,2;3,4)-diisopropylidenendioxycyclohexane (769931-79-5) + Cinnamoyl chloride (102-92-1,17082-09-6) → 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol (769931-80-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/b408467e

Reference yield:

2,2-dimethylpropanoic anhydride (1538-75-6) → 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol (769931-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / YbCl₃*6H₂O / tetrahydrofuran / 12 h / 20 °C

2: 89 percent / DMAP; pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; dmap; ytterbium(III) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b408467e

Reference yield:

1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol (40617-60-5) → 1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol (769931-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / YbCl₃*6H₂O / tetrahydrofuran / 12 h / 20 °C

2: 89 percent / DMAP; pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; dmap; ytterbium(III) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b408467e

upstream raw materials:

(1R,2R,3S,4S,5S,6R)-5-(4-pivaloyloxy)-6-hydroxy-(1,2;3,4)-diisopropylidenendioxycyclohexane

Cinnamoyl chloride

2,2-dimethylpropanoic anhydride

1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol

Downstream raw materials:

(-)-3-(phenylthio)-3-phenylpropionic acid

(-)-3-(o-aminothiophenyl)-3-phenylpropionic acid

3-(o-aminothiophenyl)-3-phenylpropionic acid

1-D-3-O-(3-phenyl-3-o-aminophenylthiopropanoyl)-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol