(E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester
• CAS No.: 136994-75-7
• Molecular Formula: C₂₃H₃₃O₉P
• Molecular Weight: 484.483
• Mol file: 136994-75-7.mol

Synonyms:

Chemical Property of (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester

There total 1 articles about (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic 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: 79.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside (102919-04-0,102854-75-1) → (E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester (136994-75-7,136994-77-9)

Guidance literature:

With 4-methyl-morpholine; titanium tetrachloride; In tetrahydrofuran; tetrachloromethane;

DOI:10.1016/S0040-4039(00)79876-5

Reference yield:

(E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester (136994-75-7,136994-77-9) → (3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (158341-64-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pd-C / ethanol

2: NaOEt / ethanol

3: 1 N NaOH / ethanol

4: Dowex 50WX₄, H₂O

With sodium hydroxide; DOWEX 50WX₄; water; hydrogen; sodium ethanolate; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)79876-5

Reference yield:

(E)-3-((3aS,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(diethoxy-phosphoryl)-acrylic acid ethyl ester (136994-75-7,136994-77-9) → (3R,4S,5S)-5-hydroxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid (90927-40-5)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10percent Pd-C / ethanol

2: NaOEt / ethanol

3: 1 N NaOH / ethanol

With sodium hydroxide; hydrogen; sodium ethanolate; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)79876-5

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

Downstream raw materials:

(3R,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

(3R,4S,5S)-5-hydroxy-3,4-(isopropylidenedioxy)cyclohex-1-enecarboxylic acid

ethyl (3R,4S,5S)-3,4-isopropylidenedioxy-5-hydroxy-cyclohex-1-ene-1-carboxylate