(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

Base Information

• Chemical Name: (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose
• CAS No.: 108182-63-4
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 108182-63-4.mol

Synonyms:(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

Chemical Property of (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

There total 4 articles about (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose 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: 90.0%

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-63-4)

Guidance literature:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate; With diisobutylaluminium hydride; In dichloromethane; toluene; at -13 ℃; for 0.833333h; Inert atmosphere;

With methanol; In dichloromethane; toluene; at -13 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.004

Reference yield: 69.0%

(E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose (72383-09-6) → (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-63-4)

Guidance literature:

With diisobutylaluminum hydride; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/0008-6215(86)80004-0

Reference yield: 62.0%

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) + allyl alcohol (107-18-6) → (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-63-4)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In water; at 25 ℃; for 48h;

DOI:10.1016/j.tetlet.2011.10.024

upstream raw materials:

(E)-5,6-didehydro-5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-heptodialo-1,4-furanose

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

Downstream raw materials:

3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxythiocarbonylamino)-α-D-gluco-hept-6-enfuranose

3-O-benzyl-5,6,7-trideoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hept-6-enfuranose

C₁₈H₂₃NO₈

methyl 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-(methoxycarbonylamino)-α-D-gluco-hexofuranuronate