D-ido-Heptonic acid,4,7-anhydro-2-deoxy-7-C-phenyl-, d-lactone, (7R)-

Base Information

• Chemical Name: D-ido-Heptonic acid,4,7-anhydro-2-deoxy-7-C-phenyl-, d-lactone, (7R)-
• CAS No.: 139626-38-3
• Molecular Formula: C13H14 O5
• Molecular Weight: 250.251
• Mol file: 139626-38-3.mol

Synonyms:2H-Furo[3,2-b]pyran,D-ido-heptonic acid deriv.; (-)-Goniofupyrone; Goniofupyrone

Chemical Property of D-ido-Heptonic acid,4,7-anhydro-2-deoxy-7-C-phenyl-, d-lactone, (7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-ido-Heptonic acid,4,7-anhydro-2-deoxy-7-C-phenyl-, d-lactone, (7R)-

There total 45 articles about D-ido-Heptonic acid,4,7-anhydro-2-deoxy-7-C-phenyl-, d-lactone, (7R)- 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: 87.0%

(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,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one (139626-38-3)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c5ob01598g

Reference yield: 82.0%

methyl (R)-3-[(2S,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-yl]-3-hydroxypropanoate (1002753-37-8) → (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one (139626-38-3)

Guidance literature:

With tris(dimethylamino) sulfonium difluorodimethylsilicate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1055/s-2007-990862

Reference yield: 74.0%

(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one (181781-56-6) → (4S,4aS,6R,7R,7aS)-4,7-dihydroxy-6-phenyl-1,5-dioxabicyclo[4.3.0]nonan-2-one (139626-38-3)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 40 ℃;

DOI:10.1016/0040-4039(96)01085-4 DOI:10.1021/jo970725u

upstream raw materials:

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

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

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

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