(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

Base Information

Chemical Name:(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one
CAS No.:247144-49-6
Molecular Formula:C₂₁H₂₃NO₄
Molecular Weight:353.418
Hs Code.:

Synonyms:(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

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Chemical Property of (3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

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Technology Process of (3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

There total 4 articles about (3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-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: 79.0%

: 100-46-9
benzylamine

: (E)-3-((2R,3R,4R)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

: 247144-49-6
(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

Guidance literature:: benzylamine; (E)-3-((2R,3R,4R)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester; With acetic acid; In methanol; at -78 ℃; for 2h;

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 24h;
DOI:10.1039/a905440e

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 247144-49-6
(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 24 percent / acetonitrile / 2 h / Heating

2.1: TFA; H₂O / 20 °C

3.1: AcOH / methanol / 2 h / -78 °C

3.2: 79 percent / NaCNBH₃; AcOH / methanol / 24 h / 20 °C

With water; acetic acid; trifluoroacetic acid; In methanol; acetonitrile; 1.1: Condensation / 2.1: Ring cleavage / 3.1: Ring cleavage / 3.2: Reduction;
DOI:10.1039/a905440e

Reference yield:

: 108788-48-3
ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 247144-49-6
(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: TFA; H₂O / 20 °C

2.1: AcOH / methanol / 2 h / -78 °C

2.2: 79 percent / NaCNBH₃; AcOH / methanol / 24 h / 20 °C

With water; acetic acid; trifluoroacetic acid; In methanol; 1.1: Ring cleavage / 2.1: Ring cleavage / 2.2: Reduction;
DOI:10.1039/a905440e