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

Base Information

• Chemical Name: (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose
• CAS No.: 108182-71-4
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359

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

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

Chemical Property:

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

There total 3 articles about (Z)-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: 88.0%

ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-48-3) → (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-71-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; for 3h; Ambient temperature;

DOI:10.1248/cpb.34.3102

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / methanol / 4 h / 0 °C

2: lithium aluminium hydride / tetrahydrofuran / 5 h / Ambient temperature

With lithium aluminium tetrahydride; In tetrahydrofuran; methanol;

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

Reference yield:

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate (108266-98-4) → (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose (108182-71-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Ambient temperature;

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

upstream raw materials:

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

methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate

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

Downstream raw materials:

(Z)-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)-allyl diethyl phosphate

6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-D-glycero-L-ido-heptofuranose

6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-7-O-p-toluenesulfonyl-α-L-glycero-D-gluco-heptofuranose

6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-L-ido-heptofuranose

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