(E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate

Base Information

• Chemical Name: (E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate
• CAS No.: 895140-23-5
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385

Synonyms:(E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate

Chemical Property of (E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate

There total 1 articles about (E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate 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: 92.0%

(2E)-6-O-benzyl-2,3-dideoxy-4,5-O-(1-methylethylidene)-D-threo-hex-2-enitol + methyl chloroformate (79-22-1) → (E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate (895140-23-5)

Guidance literature:

(2E)-6-O-benzyl-2,3-dideoxy-4,5-O-(1-methylethylidene)-D-threo-hex-2-enitol; methyl chloroformate; With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;

With ammonium chloride; In dichloromethane; at 20 ℃;

DOI:10.1002/adsc.200505140

Reference yield:

(E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate (895140-23-5) + tert-butyl N-(trifluoroacetyl)glycinate (63959-88-6) → tert-butyl (E)-(2S,6R,7R)-2-(trifluoroacetyl)amino-8-benzyloxy-6,7-O-isopropylidene-6,7-dihydroxy-4-octenoate + tert-butyl (E)-(2R,6R,7R)-2-(trifluoroacetyl)amino-8-benzyloxy-6,7-O-isopropylidene-6,7-dihydroxy-4-octenoate

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/anie.200500095

Reference yield:

(E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate (895140-23-5) + C8H10F3NO3(2-)*Zn(2+) → tert-butyl (E)-(2S,6R,7R)-2-(trifluoroacetyl)amino-8-benzyloxy-6,7-O-isopropylidene-6,7-dihydroxy-4-octenoate + tert-butyl (E)-(2R,6R,7R)-2-(trifluoroacetyl)amino-8-benzyloxy-6,7-O-isopropylidene-6,7-dihydroxy-4-octenoate

Guidance literature:

(E)-(4R,5R)-6-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-2-hexen-1-yl methyl carbonate; C₈H₁₀F₃NO₃^(2-)*Zn⁽²⁺⁾; With triphenylphosphine; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at -78 - 20 ℃; for 12h;

With ammonium chloride; In tetrahydrofuran; diethyl ether; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1002/adsc.200505140

upstream raw materials:

methyl chloroformate

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