1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate

Base Information

• Chemical Name: 1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate
• CAS No.: 109680-99-1
• Molecular Formula: C30H31NO7
• Molecular Weight: 517.56964
• Mol file: 109680-99-1.mol

Synonyms:1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate;1,2-O-(1-Isopropyldene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate;5-OxiMe-5-deoxy-1,2-isopropyldene-6-O-trityl-α-D-galactofuranose 3-Acetate

Chemical Property of 1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate

Chemical Property:

• PSA: 95.81000
• LogP: 4.63340

Purity/Quality:

95% ^*data from raw suppliers

1,2-O-(1-Methylethylidene)-6-O-(triphenylmethyl)-β-L-arabino-hexofuranos-5-uloseOxime3-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Galactostatin (G156500) intermediate.

Technology Process of 1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate

There total 5 articles about 1,2-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-β-L-arabino-hexofuranos-5-ulose OxiMe 3-Acetate 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%

3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose (109680-98-0) → Acetic acid (3aR,5S,6S,6aR)-5-{1-[(Z)-hydroxyimino]-2-trityloxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (109680-99-1)

Guidance literature:

With hydroxylamine hydrochloride; potassium hydrogencarbonate; In methanol; Heating;

DOI:10.1016/S0008-6215(00)90138-1

Reference yield:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose (38166-65-3) → Acetic acid (3aR,5S,6S,6aR)-5-{1-[(Z)-hydroxyimino]-2-trityloxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (109680-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 50percent aq. AcOH / 5 h / Ambient temperature; concentrated at 25 deg C

2: 98 percent / pyridine / 7 h / 70 °C

3: 95 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 1 h / Heating

4: 96 percent / hydroxylammonium chloride, KHCO₃ / methanol / Heating

With pyridine; dipyridinium dichromate; hydroxylamine hydrochloride; acetic anhydride; potassium hydrogencarbonate; acetic acid; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90138-1

Reference yield:

3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-α-D-galactofuranose (109680-97-9) → Acetic acid (3aR,5S,6S,6aR)-5-{1-[(Z)-hydroxyimino]-2-trityloxy-ethyl}-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (109680-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂ / 1 h / Heating

2: 96 percent / hydroxylammonium chloride, KHCO₃ / methanol / Heating

With dipyridinium dichromate; hydroxylamine hydrochloride; acetic anhydride; potassium hydrogencarbonate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90138-1

upstream raw materials:

3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-β-L-arabino-hexofuranos-5-ulose

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose

3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-α-D-galactofuranose

3-O-acetyl-1,2-O-isopropylidene-α-D-galactofuranose

Downstream raw materials:

5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-β-L-altrofuranose

5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-α-D-galactofuranose