methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate

Base Information

• Chemical Name: methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate
• CAS No.: 874460-63-6
• Molecular Formula: C₁₈H₁₉NO₇S
• Molecular Weight: 393.417
• Mol file: 874460-63-6.mol

Synonyms:methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate

Chemical Property of methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate

There total 5 articles about methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate 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: 80.0%

thiophosgene (463-71-8) + methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α,β-D-arabino-hex-2-ulopyranosyl amine)onate → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate + methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate (874460-63-6)

Guidance literature:

With calcium carbonate; In water; at 20 ℃; for 72h;

DOI:10.1016/j.tet.2005.09.128

Reference yield:

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane (364635-35-8) → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate (874460-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / tetrabutyl ammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

2: ruthenium(III) chloride hydrate; sodium metaperiodate / acetonitrile; H₂O; CCl₄ / 0.25 h / 20 °C

3: 0.17 percent / methanol; diethyl ether / 0.33 h / 0 °C

4: 70 percent / hydrogen / palladium on carbon / methanol / 1 h / 20 °C

5: 80 percent / CaCO₃ / H₂O / 72 h / 20 °C

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; acetonitrile;

DOI:10.1016/j.tet.2005.09.128

Reference yield:

methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate (874460-60-3) → methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate (874460-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / hydrogen / palladium on carbon / methanol / 1 h / 20 °C

2: 80 percent / CaCO₃ / H₂O / 72 h / 20 °C

With hydrogen; calcium carbonate; palladium on activated charcoal; In methanol; water;

DOI:10.1016/j.tet.2005.09.128

upstream raw materials:

thiophosgene

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

2-azido-3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate