3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose

Base Information

• Chemical Name: 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose
• CAS No.: 195519-71-2
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 195519-71-2.mol

Synonyms:3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose

Chemical Property of 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose

There total 3 articles about 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-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: 93.0%

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose (195519-71-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.01.007

Reference yield: 85.0%

(1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (72277-35-1) → 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose (195519-71-2)

Guidance literature:

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h;

DOI:10.1002/hlca.19970800517

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose (195519-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / tetrahydrofuran / 2 h / Ambient temperature

2: 85 percent / DIBAH, BF₃*Et₂O / CH₂Cl₂; toluene / 1 h / -78 °C

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/hlca.19970800517

upstream raw materials:

(1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

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

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

Downstream raw materials:

3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose

3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-α-D-glycero-L-ido-hepto-1,4-furanose