3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one

Base Information

• Chemical Name: 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one
• CAS No.: 221017-83-0
• Molecular Formula: C₂₄H₂₂O₇
• Molecular Weight: 422.434

Synonyms:3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one

Chemical Property of 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one

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Technology Process of 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one

There total 1 articles about 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one 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: 65.0%

salicylaldehyde (90-02-8) + ethyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate-5-ulose (161144-16-7) → 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one (221017-83-0) + (Z)-2-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbonyl)-3-(2-hydroxy-phenyl)-acrylic acid ethyl ester

Guidance literature:

With piperidine; molecular sieve; In ethanol; at 70 ℃; for 0.333333h; Product distribution; other substrate: ethyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-ribo-heptofuranuronate-5-ulose, other 2-hydroxy benzaldehydes, other reagents: KF, Et3N, iPrNH2, Cs2CO3, pyrrolidine, DBU, SiO2, Al2O3, CdI2, other temperature, other solvents;

DOI:10.1021/jo981868z

Reference yield: 80.0%

3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one (221017-83-0) → 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-3,4-dihydro-2H-1-benzopyran-2-one

Guidance literature:

With sodium tetrahydroborate; In 2-methoxy-ethanol; at -78 ℃; for 0.5h;

DOI:10.1021/jo981868z

Reference yield: 80.0%

3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-pentofuran-5-ulose)>-2H-1-benzopyran-2-one (221017-83-0) → 3-<5-(1,2-O-isopropylidene-3-O-benzyl-α-D-gluco-pentofuranose)>-2H-1-benzopyran-2-one + 3-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-chromen-2-one

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 0.5h; Mechanism;

DOI:10.1021/jo981868z

upstream raw materials:

salicylaldehyde

ethyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-heptofuranuronate-5-ulose

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