(2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

Base Information

• Chemical Name: (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one
• CAS No.: 181534-69-0
• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.361
• Mol file: 181534-69-0.mol

Synonyms:(2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

Chemical Property of (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

There total 21 articles about (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-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: 89.0%

Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester (181534-74-7) → (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one (181534-69-0)

Guidance literature:

With hydrogen fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4039(96)01085-4

Reference yield: 82.0%

methyl (3R)-3-((2S,3S,4R,5R)-4-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-phenyltetrahydrofuran-2-yl)-3-methoxypropanoate → (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one (181534-69-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c5ob01598g

Reference yield: 73.0%

(2R,3R,3aS,7R,7aS)-3-(benzyloxy)-7-hydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one (181534-71-4) → (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one (181534-69-0)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 85 ℃; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.200800535

upstream raw materials:

Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

(5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one

(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

Downstream raw materials:

goniothalenol

(2R,3R,3aS,6S,7R,7aS)-3-Benzyloxy-6,7-dihydroxy-2-phenyl-hexahydro-furo[3,2-b]pyran-5-one

(2R,3R,3aS,7R,7aS)-3-Benzyloxy-5-methoxy-2-phenyl-hexahydro-furo[3,2-b]pyran-7-ol

(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one