methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

Base Information

Chemical Name:methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate
CAS No.:404377-32-8
Molecular Formula:C₃₆H₃₈O₇
Molecular Weight:582.694
Hs Code.:

Synonyms:methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

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Chemical Property of methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

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Technology Process of methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

There total 8 articles about methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate 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: 64.0%

: 404377-30-6
methyl 2,4,5,7-tetra-O-benzyl-3-O-thiobenzoyl-α-D-gluco-2-heptulopyranosonate

: 404377-32-8
methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 20 - 90 ℃; for 4h;
DOI:10.1002/1099-0690(20021)2002:1<57::AID-EJOC57<3.0.CO;2-H

Reference yield:

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 404377-32-8
methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

1.2: 79 percent / MgBr₂ / tetrahydrofuran; hexane / 3 h / 0 - 20 °C

2.1: 73 percent / N-iodosuccinimide / acetone / 0.5 h / 20 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 1.5 h

4.1: NaH / dimethylformamide / 2 h / 20 °C

5.1: 485 mg / NaOMe / methanol / 2 h / 20 °C

6.1: pyridine / CH₂Cl₂ / 20 °C

7.1: 555 mg / H₂S / CH₂Cl₂ / 0.17 h

8.1: 64 percent / Bu₃SnH; AIBN / toluene / 4 h / 20 - 90 °C

With pyridine; N-iodo-succinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen sulfide; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/1099-0690(20021)2002:1<57::AID-EJOC57<3.0.CO;2-H

Reference yield:

: 136305-59-4
methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate

: 404377-32-8
methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / pyridine / CH₂Cl₂ / 1.5 h

2: NaH / dimethylformamide / 2 h / 20 °C

3: 485 mg / NaOMe / methanol / 2 h / 20 °C

4: pyridine / CH₂Cl₂ / 20 °C

5: 555 mg / H₂S / CH₂Cl₂ / 0.17 h

6: 64 percent / Bu₃SnH; AIBN / toluene / 4 h / 20 - 90 °C

With pyridine; 2,2'-azobis(isobutyronitrile); hydrogen sulfide; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/1099-0690(20021)2002:1<57::AID-EJOC57<3.0.CO;2-H