(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester

Base Information

• Chemical Name: (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester
• CAS No.: 114340-89-5
• Molecular Formula: C₁₉H₂₆O₇
• Molecular Weight: 366.411
• Mol file: 114340-89-5.mol

Synonyms:(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester

Chemical Property of (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester

There total 2 articles about (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester 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: 85.0%

ethyl bromoacetate (105-36-2) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester (114340-89-5)

Guidance literature:

DOI:10.1016/S0040-4039(00)96427-X

Reference yield:

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (908142-25-6) → (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester (114340-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaIO₄ / ethanol; H₂O / 0.5 h / Ambient temperature

2: 85 percent / Zn / benzene; diethyl ether / 0.5 h / Heating

With sodium periodate; zinc; In diethyl ether; ethanol; water; benzene;

DOI:10.1016/S0040-4020(01)80093-4

Reference yield:

(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid ethyl ester (114340-89-5) → (5R,6S)-5-Hydroxy-6-((S)-1-hydroxy-2,2-diphenyl-ethyl)-5,6-dihydro-pyran-2-one (114340-94-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1N NaOH / H₂O

2: H₂ / Pd/C 10percent / ethyl acetate / 760 Torr

3: 1.) dicyclohexylcarbodiimide / 2.) 4-dimethylaminopyridine / 1.) pyridine, RT, 6 h; 2.) RT, overnight

4: 87 percent / diazabicycloundecene / CH₂Cl₂ / 1 h / Ambient temperature

5: 3.4 percent / HF / 0.17 h / 0 °C

With sodium hydroxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; hydrogen fluoride; In dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(01)80093-4

upstream raw materials:

ethyl bromoacetate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

Downstream raw materials:

(S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid

(5R,6S)-5-Hydroxy-6-((S)-1-hydroxy-2,2-diphenyl-ethyl)-5,6-dihydro-pyran-2-one

(2R,3S,3aR,7aR)-3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

(-) Altholactone