benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

Base Information

Chemical Name:benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate
CAS No.:1569902-41-5
Molecular Formula:C₂₆H₃₁IO₈
Molecular Weight:598.432
Hs Code.:

Synonyms:benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

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Chemical Property of benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

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Technology Process of benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

There total 15 articles about benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)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:

: 67-56-1
methanol

: 1569902-13-1
benzyl 2,6-anhydro-8-O-benzyl-3-deoxy-4,5-O-isopropylidene-D-manno-oct-2-enosonate

: 1569902-41-5
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

: 1569902-43-7
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-α-D-galacto-2-octulopyranoside)onate

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -45 ℃; for 4h; Overall yield = 70 %; Overall yield = 951 mg; Molecular sieve;
DOI:10.1021/ol500275j

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 1569902-41-5
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

: 1569902-43-7
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-α-D-galacto-2-octulopyranoside)onate

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 19 h / -40 - 0 °C / Inert atmosphere

2.1: cesium fluoride / acetonitrile; water / 2 h / 0 - 20 °C

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

5.1: magnesium sulfate; sodium hydrogencarbonate / water / 0.5 h / 20 °C

5.2: 4 h / 0 °C

6.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 10 h

7.1: dmap / acetonitrile / 0 °C

8.1: triethyl phosphite / 2.5 h / 120 °C

9.1: zinc(II) nitrate hexahydrate / acetonitrile / 12 h / 50 °C

10.1: toluene / 3 h / Reflux; Dean-Stark

11.1: cesium fluoride / toluene; acetonitrile / 10 h / 20 - 70 °C

12.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / 4 h / -45 °C / Molecular sieve

With dmap; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; zinc(II) nitrate hexahydrate; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; silver nitrate; cesium fluoride; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol500275j

Reference yield:

: 1569902-07-3
3,6-di-O-benzyl-1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-1-yno-octitol

: 1569902-41-5
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranoside)onate

: 1569902-43-7
benzyl (methyl 8-O-benzyl-4,5-O-isopropylidene-3-deoxy-3-iodo-D-glycero-α-D-galacto-2-octulopyranoside)onate

Guidance literature:: Multi-step reaction with 11 steps

1.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

2.1: magnesium sulfate; sodium hydrogencarbonate / water / 0.5 h / 20 °C

2.2: 4 h / 0 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 10 h

4.1: dmap / acetonitrile / 0 °C

5.1: triethyl phosphite / 2.5 h / 120 °C

6.1: zinc(II) nitrate hexahydrate / acetonitrile / 12 h / 50 °C

7.1: toluene / 3 h / Reflux; Dean-Stark

8.1: cesium fluoride / toluene; acetonitrile / 10 h / 20 - 70 °C

9.1: lithium hydroxide / methanol; tetrahydrofuran; water / 0.5 h / 0 - 20 °C

10.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

11.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / 4 h / -45 °C / Molecular sieve

With dmap; N-Bromosuccinimide; N-iodo-succinimide; zinc(II) nitrate hexahydrate; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; magnesium sulfate; potassium carbonate; silver nitrate; cesium fluoride; lithium hydroxide; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ol500275j