5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

Base Information

• Chemical Name: 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one
• CAS No.: 899436-62-5
• Molecular Formula: C₂₇H₂₈O₆
• Molecular Weight: 448.516
• Mol file: 899436-62-5.mol

Synonyms:5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

Chemical Property of 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

There total 28 articles about 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-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: 98.0%

methyl 2-((4R,5S)-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)acetate (917079-00-6) → 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one (899436-62-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; for 24h;

DOI:10.1016/j.tet.2006.09.005

Reference yield: 80.0%

(R)-3-[(4S,5R,6R)-5-Benzyloxy-6-((R)-benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-propionic acid ethyl ester (899436-55-6) → 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one (899436-62-5)

Guidance literature:

With acetic acid; for 8h;

DOI:10.1016/j.tetlet.2006.04.146

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose (18439-43-5,18439-42-4) → 5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one (899436-62-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / NaH; TBAI / tetrahydrofuran / 2 h / 20 °C

2: 80 percent / H₂SO₄ / dioxane; H₂O / 20 h / 100 °C

3: 98 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

4: 98 percent / CH₂Cl₂ / 2 h / 20 °C

5: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

7: 92 percent / AD-mix β; (DHQD)2PHAL; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

8: CSA / CH₂Cl₂ / 2 h / 20 °C

9: 91 percent / lithium hydroxide monohydrate / methanol; H₂O / 2 h / 25 °C

10: triethylamine; ethylchloroformate / tetrahydrofuran / 0.75 h / 0 - 20 °C

11: 453.7 mg / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C

12: 68 percent / silver benzoate; triethylamine / 1.5 h / cooling

13: 98 percent / TFA / CH₂Cl₂; H₂O / 24 h

With 2,6-dimethylpyridine; lithium hydroxide; sodium periodate; methanesulfonamide; sulfuric acid; camphor-10-sulfonic acid; silver benzoate; chloroformic acid ethyl ester; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; tert-butyl alcohol; 4: Wittig olefination / 7: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2006.09.005

upstream raw materials:

(R)-3-[(4S,5R,6R)-5-Benzyloxy-6-((R)-benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-propionic acid ethyl ester

methyl 2-((4R,5S)-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)acetate

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate