(3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

Base Information

• Chemical Name: (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol
• CAS No.: 18439-35-5
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 18439-35-5.mol

Synonyms:(3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

Chemical Property of (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

There total 15 articles about (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol 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%

((3aR,5S,6R,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanone → (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol (18439-35-5) + (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol (18439-34-4)

Guidance literature:

With sodium tetrahydroborate; silica gel; In hexane; at 22 ℃; for 28h; Reagent/catalyst; Solvent; Temperature; stereoselective reaction;

DOI:10.1016/j.tet.2015.05.040

Reference yield: 83.0%

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (18439-43-5,18439-42-4) → (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol (18439-35-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 23h; under 760.051 Torr;

DOI:10.1016/j.tet.2015.05.040

Reference yield: 59.0%

bromobenzene (108-86-1,52753-63-6) + 3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose (152185-56-3) → (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol (18439-35-5) + (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol (18439-34-4)

Guidance literature:

bromobenzene; With magnesium; In tetrahydrofuran; at 20 ℃; for 0.5h;

3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose; In tetrahydrofuran; at 0 - 20 ℃; for 10h;

With water; ammonium chloride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2010.10.016

upstream raw materials:

bromobenzene

1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(+)-goniofufurone

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose

(5R,SP)-1,2-O-isopropylidene-5-phenyl-3,5-O-(5'-(2',3'-O-isopropiliden-5-metyluridinyl))phosphoryl-α-D-xylofuranose

(5R,RP)-1,2-O-isopropylidene-5-phenyl-3,5-O-(5'-(2',3'-O-isopropiliden-5-metyluridinyl))phosphoryl-α-D-xylofuranose