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

Base Information

• Chemical Name: phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside
• CAS No.: 162332-28-7
• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.491
• Mol file: 162332-28-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside 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: 96.0%

tert-butyl acetoacetate (1694-31-1) + benzyl 2,3-anhydro-4-O-methoxymethyl-β-L-ribopyranoside → phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside (162332-28-7)

Guidance literature:

tert-butyl acetoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.75h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; hexane; mineral oil; at 0 ℃; for 0.666667h; Inert atmosphere;

benzyl 2,3-anhydro-4-O-methoxymethyl-β-L-ribopyranoside; In tetrahydrofuran; hexane; mineral oil; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo900192a

Reference yield:

methanesulfonyl chloride (124-63-0) + phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside (162332-28-7) → 4-((2S,3S,4R,5R)-2-Benzyloxy-3-methanesulfonyloxy-5-methoxymethoxy-tetrahydro-pyran-4-yl)-3-oxo-butyric acid tert-butyl ester

Guidance literature:

With triethylamine; In dichloromethane; at -15 ℃; for 1h;

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

Reference yield:

methanesulfonyl chloride (124-63-0) + phenylmethyl 3-deoxy-3-[4-(1,1-dimethylethoxy)-2,4-dioxobutyl]-4-O-(methoxymethyl)-β-L-xylopyranoside (162332-28-7) → 4-((2S,4R,5R)-2-Benzyloxy-3-methanesulfonyloxy-5-methoxymethoxy-tetrahydro-pyran-4-yl)-3-oxo-butyric acid tert-butyl ester

Guidance literature:

With triethylamine; In dichloromethane; at -15 ℃; for 2h;

upstream raw materials:

tert-butyl acetoacetate

Downstream raw materials:

[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