2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester

Base Information

• Chemical Name: 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester
• CAS No.: 152715-16-7
• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.406
• Mol file: 152715-16-7.mol

Synonyms:

Chemical Property of 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester

There total 2 articles about 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl 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) → 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (152715-16-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: piperidine / toluene / 3 h / -78 °C

With sodium periodate; piperidine; In methanol; water; toluene;

DOI:10.1016/S0040-4020(01)87984-9

Reference yield:

acetoacetic acid methyl ester (105-45-3) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (152715-16-7)

Guidance literature:

piperidine; In toluene; at -78 ℃; for 3h;

DOI:10.1016/S0040-4020(01)87984-9

Reference yield:

2-[1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (152715-16-7) + malononitrile (109-77-3) → 6-Amino-4-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-5-cyano-2-methyl-4H-pyran-3-carboxylic acid methyl ester

Guidance literature:

piperidine; In toluene; Yield given; -78 deg C, then room t., 24 h;

DOI:10.1016/S0040-4020(01)87984-9

upstream raw materials:

acetoacetic acid methyl ester

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

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