(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 38714-70-4
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• Mol file: 38714-70-4.mol

Synonyms:(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 20 articles about (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 78.0%

para-iodoanisole (696-62-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (38714-70-4)

Guidance literature:

With bis(acetylacetonate)nickel(II); magnesium chloride; In tetrahydrofuran; at 15 ℃; stereoselective reaction;

DOI:10.1007/s11426-019-9501-4

Reference yield: 52.0%

4-methoxyphenyl magnesium bromide (13139-86-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (38714-70-4)

Guidance literature:

4-methoxyphenyl magnesium bromide; 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; In diethyl ether; for 1h; Heating;

With pyridine; acetic anhydride; at 20 ℃; for 12h;

DOI:10.3390/10080843

Reference yield: 11.0%

4-MeOC6H4ZnI*LiCl + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester (38714-71-5) + (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (38714-70-4) + D-glucal triacetate (2873-29-2)

Guidance literature:

With bis (1,5-cyclopentadiene)nickel ⁽⁰⁾; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In N,N-dimethyl-formamide; at 25 ℃; for 12h; optical yield given as %de;

DOI:10.1021/ja8041564

upstream raw materials:

4-methoxyphenyl magnesium bromide

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride

acetic anhydride

2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-methoxyphenyl)-β-D-glucopyranose

Downstream raw materials:

(1S)-1,5-anhydro-1-(4-methoxyphenyl)-D-glucitol

4-(2,3,4-tri-O-acetyl-6-desoxy-β-D-xylo-hex-5-enopyranosyl)anisole

4-(2,3,4-tri-O-acetyl-6-desoxy-6-iodo-β-D-glucopyranosyl)anisole

4-(2,3,4-tri-O-benzyl-6-desoxy-β-D-xylo-hex-5-enopyranosyl)anisole