[3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester
• CAS No.: 162332-31-2
• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.476
• Mol file: 162332-31-2.mol

Synonyms:

Chemical Property of [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester

There total 4 articles about [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl 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:

4-((2S,3S,4R,5R)-2-Benzyloxy-3-methanesulfonyloxy-5-methoxymethoxy-tetrahydro-pyran-4-yl)-3-oxo-butyric acid tert-butyl ester → [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester (162332-31-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 5h;

DOI:10.1016/0040-4039(94)02309-Y

Reference yield:

phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside (162332-28-7) → [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester (162332-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h / -15 °C

2: NaH / tetrahydrofuran / 5 h / 0 - 25 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(94)02309-Y

Reference yield:

benzyl 2,3-anhydro-4-O-methoxymethyl-β-L-ribopyranoside → [3aR-(2Z,3aα,4α,7β,7aα)]-[hexahydro-4-(methoxymethoxy)-7-(phenylmethoxy)-2H-furo[2,3-c]pyran-2-ylidene]-acetic acid 1,1-dimethylethyl ester (162332-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH, n-BuLi / tetrahydrofuran / 6 h / 0 - 25 °C

2: Et₃N / CH₂Cl₂ / 1 h / -15 °C

3: NaH / tetrahydrofuran / 5 h / 0 - 25 °C

With n-butyllithium; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(94)02309-Y

upstream raw materials:

phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside