(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester

Base Information

• Chemical Name: (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester
• CAS No.: 160906-15-0
• Molecular Formula: C₂₆H₄₀O₇Si
• Molecular Weight: 492.685
• Mol file: 160906-15-0.mol

Synonyms:

Chemical Property of (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester

There total 4 articles about (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic 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:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester (160906-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1: imid / CH₂Cl₂ / 3 h / Ambient temperature

2: DMSO, (COCl)2, Et₃N / biphenyl / 1 h / -78 °C

3: CH₂Cl₂ / 18 h / Ambient temperature

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In biphenyl; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester (160906-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.8 percent H₂SO₄ / methanol / 12 h / Ambient temperature

2: imid / CH₂Cl₂ / 3 h / Ambient temperature

3: DMSO, (COCl)2, Et₃N / biphenyl / 1 h / -78 °C

4: CH₂Cl₂ / 18 h / Ambient temperature

With 1H-imidazole; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; In methanol; biphenyl; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

Reference yield:

1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9) → (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid ethyl ester (160906-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO, (COCl)2, Et₃N / biphenyl / 1 h / -78 °C

2: CH₂Cl₂ / 18 h / Ambient temperature

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In biphenyl; dichloromethane;

DOI:10.1016/S0040-4039(00)76809-2

upstream raw materials:

3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

ethyl (triphenylphosphoranylidene)acetate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

(R)-((1S,3S,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester

(S)-((1S,3R,4S,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-6-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-3-yl)-hydroxy-acetic acid ethyl ester

(Z)-4-Benzyloxy-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enoic acid ethyl ester