3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Base Information

• Chemical Name: 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
• CAS No.: 107207-19-2
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 107207-19-2.mol

Synonyms:3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Chemical Property of 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose

There total 4 articles about 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose 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:

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose (109536-51-8,142226-16-2,69940-04-1) → 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (107207-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1: C₅H₅N / CH₂Cl₂ / -65 °C

2: LiAlH / tetrahydrofuran / 1.) r.t.; 2.) reflux

3: 1.) DMSO; 2.) NEt₃ / 1.) TFA anhydride, CH₂Cl₂, -65 deg C; 2.) -65 deg C

With pyridine; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1246/cl.1989.1

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose (115693-78-2,142226-15-1,69940-02-9) → 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (107207-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: HOAc / H₂O / Ambient temperature

2: C₅H₅N / CH₂Cl₂ / -65 °C

3: LiAlH / tetrahydrofuran / 1.) r.t.; 2.) reflux

4: 1.) DMSO; 2.) NEt₃ / 1.) TFA anhydride, CH₂Cl₂, -65 deg C; 2.) -65 deg C

With pyridine; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1246/cl.1989.1

Reference yield:

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-O-(p-tolylsulfonyl)-α-D-glucofuranose (82530-09-4) → 3-O-(4-methoxybenzyl)-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (107207-19-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH / tetrahydrofuran / 1.) r.t.; 2.) reflux

2: 1.) DMSO; 2.) NEt₃ / 1.) TFA anhydride, CH₂Cl₂, -65 deg C; 2.) -65 deg C

With dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1246/cl.1989.1

upstream raw materials:

(R)-1-[(3aR,5R,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethanol

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-O-(p-tolylsulfonyl)-α-D-glucofuranose

Downstream raw materials:

ethyl 6-deoxy-1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-α-D-xylo-hept-5-ulofuranuronate

4-methoxy-benzaldehyde

6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranosid-5-ulose

(6S)-3,6-anhydro-1,2-O-isopropylidene-5-C-methyl-6-C-(4-methoxyphenyl)-α-D-glucofuranose