(2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester
• CAS No.: 38714-71-5
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• Mol file: 38714-71-5.mol

Synonyms:(2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester

Chemical Property of (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-yl ester

There total 13 articles about (2R,3R,4R,5S,6R)-acetic acid 4,5-diacetoxy-2-acetoxymethyl-6-(4-methoxyphenyl)tetrahydropyran-3-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: 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

Reference yield:

1-bromo-4-methoxy-benzene (104-92-7) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride (4451-36-9) → (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)

Guidance literature:

With nickel(II) bromide dimethoxyethane; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine; In acetonitrile; at 25 ℃; for 24h; Overall yield = 58 percent; diastereoselective reaction; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1002/adsc.202100343

Reference yield:

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,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)

Guidance literature:

With cobalt(III) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Overall yield = 83 %; diastereoselective reaction;

DOI:10.1002/anie.201204786 DOI:10.1002/anie.201204786

upstream raw materials:

1-bromo-4-methoxy-benzene

(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol

((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-(4-methoxy-phenyl)-dimethyl-silane

((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane