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

Base Information

• Chemical Name: methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate
• CAS No.: 108266-98-4
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369

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

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

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

There total 7 articles about methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate 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: 89.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate (108266-98-4)

Guidance literature:

In methanol; at 0 ℃; for 4h;

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

Reference yield: 42.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate (77399-49-6) + methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate (108266-98-4)

Guidance literature:

In benzene; for 4h; Heating;

DOI:10.1016/j.tetlet.2004.06.017

Reference yield:

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (591727-19-4) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate (77399-49-6) + methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-5-enofuranuronate (108266-98-4)

Guidance literature:

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose; With water; acetic acid; for 24h;

With sodium periodate; for 2h;

methyl (triphenylphosphoranylidene)acetate; In toluene; at 25 ℃; for 2h; optical yield given as %de;

DOI:10.1039/c1gc15097a

upstream raw materials:

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

methyl (triphenylphosphoranylidene)acetate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

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

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-L-ido-heptofuranuronate

(2aR,4aR,5R,6S,6aS,6bR)-1-Benzyl-5-benzyloxy-6-hydroxy-hexahydro-2,4-dioxa-1-aza-cyclopenta[cd]pentalen-3-one

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