(E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate

Base Information

• Chemical Name: (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate
• CAS No.: 102487-47-8
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• Mol file: 102487-47-8.mol

Synonyms:(E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate

Chemical Property of (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate

There total 15 articles about (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate 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%

3,5-di-O-benzyl-D-xylofuranose (16054-77-6,120693-82-5,120693-83-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate (102487-47-8)

Guidance literature:

In toluene; for 0.5h; Heating;

DOI:10.1016/S0040-4039(00)98773-2

Reference yield: 66.0%

3,5-di-O-benzyl-D-xylofuranose (16054-77-6,120693-82-5,120693-83-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate (102487-47-8) + 3,6-anhydro-5,7-di-O-benzyl-2-deoxy-D-ido-heptono-1,4-lactone (279221-72-6)

Guidance literature:

In benzene; for 24h; Reflux;

DOI:10.2298/JSC200730056S

Reference yield:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (41341-99-5) → (E,4S,5R,6R)-methyl 5,7-di(benzyloxy)-4,6-dihydroxy-2-heptenoate (102487-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / 12 M HCl, AcOH / 0.08 h / Ambient temperature

2: 92 percent / toluene / 0.01 h / Heating

With hydrogenchloride; acetic acid; In toluene;

DOI:10.1016/S0040-4020(01)86175-5

upstream raw materials:

3,5-di-O-benzyl-L-xylofuranose

methyl (triphenylphosphoranylidene)acetate

(3aS,5S,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)dimethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole

L-(-)-xylose

Downstream raw materials:

3-((4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-[1,3]dioxan-4-yl)-pentanedioic acid dimethyl ester

(1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2S)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one

(1R,2S,6R,7R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(1R,2R)-1-hydroxy-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2.7>tridecan-11-one