[(4aR,6S,7R,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate

Base Information

• Chemical Name: [(4aR,6S,7R,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS No.: 18031-57-7
• Molecular Formula: C16H20O7
• Molecular Weight: 324.331
• Nikkaji Number: J981.791C
• Mol file: 18031-57-7.mol

Synonyms:SCHEMBL7151517

Chemical Property of [(4aR,6S,7R,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate

Chemical Property:

• Vapor Pressure: 1.9E-09mmHg at 25°C
• Boiling Point: 465.1°Cat760mmHg
• Flash Point: 168.5°C
• Density: 1.32g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 324.12090297
• Heavy Atom Count: 23
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC2C1OC(OC2)C3=CC=CC=C3)OC)O
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H]([C@H](O[C@H]2[C@H]1OC(OC2)C3=CC=CC=C3)OC)O

Technology Process of [(4aR,6S,7R,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate

There total 52 articles about [(4aR,6S,7R,8R,8aR)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 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: 95.0%

Acetic acid (2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-prop-2-ynyloxycarbonyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (488743-95-9) → methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (2872-56-2,18031-57-7,20750-03-2,37180-50-0,37180-54-4,87924-30-9,96779-62-3,104321-10-0,130464-35-6,141611-59-8,144607-25-0,144607-28-3,150654-17-4)

Guidance literature:

With tetrathiomolybdate(VI); In acetonitrile; at 28 ℃; for 3h;

DOI:10.1021/ol027220x

Reference yield: 93.0%

methyl 3-O-acetyl-4,6-O-benzylidene-2-O-(N-phenylcarbamoyl)-α-D-glucopyranoside → methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (2872-56-2,18031-57-7,20750-03-2,37180-50-0,37180-54-4,87924-30-9,96779-62-3,104321-10-0,130464-35-6,141611-59-8,144607-25-0,144607-28-3,150654-17-4)

Guidance literature:

With pyridine; acetic anhydride; tetrabutylammonium nitrite; 0 deg C, 10 min, then 40 deg C, 2 h;

DOI:10.1016/S0040-4039(98)01126-5

Reference yield: 92.0%

Acetic acid (2R,4aR,6S,7R,8S,8aR)-7-allyloxycarbonyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (162226-16-6) → methyl 3-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (2872-56-2,18031-57-7,20750-03-2,37180-50-0,37180-54-4,87924-30-9,96779-62-3,104321-10-0,130464-35-6,141611-59-8,144607-25-0,144607-28-3,150654-17-4)

Guidance literature:

With formic acid; tributylphosphine; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 70 ℃; for 0.166667h;

upstream raw materials:

acetic anhydride

methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside]

pyridine

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Downstream raw materials:

methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-methanesulfonyl-α-D-glucopyranoside]

methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-(toluene-4-sulfonyl)-α-D-glucopyranoside]

methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-trifluoroacetyl-α-D-glucopyranoside]

methyl-[O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O²-methyl-α-D-glucopyranoside]