1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

Base Information

Chemical Name:1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose
CAS No.:1378358-27-0
Molecular Formula:C₃₅H₄₀O₈
Molecular Weight:588.698
Hs Code.:

Synonyms:1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

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Chemical Property of 1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

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Technology Process of 1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

There total 12 articles about 1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose 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:

: 1378358-24-7
1,6,7-tri-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranoside

: 762-72-1
allyl-trimethyl-silane

: 1378358-27-0
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

: 1378358-25-8
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranose

Guidance literature:: 1,6,7-tri-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranoside; allyl-trimethyl-silane; With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 3h;

With sodium hydrogencarbonate; In water; acetonitrile; pH=7;

Reference yield:

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

: 1378358-27-0
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

: 1378358-25-8
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranose

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium; methanol / 2 h / Inert atmosphere

1.2: IR-120 (Amberlite H form)

2.1: 1H-imidazole / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; methanol / 1.66 h / 0 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / water; tetrahydrofuran / 2 h / Inert atmosphere

5.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -70 °C / Inert atmosphere

5.2: 0.25 h

6.1: Methyltriphenylphosphonium bromide; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

7.1: potassium carbonate; potassium osmate(VI); tripotassium hexacyanoferrate / toluene; water; tert-butyl alcohol / 96 h / 0 °C

8.1: dmap; pyridine / 20 °C

9.1: N-Bromosuccinimide / acetonitrile / 6 h / -15 °C

9.2: 6 h / 20 °C

10.1: boron trifluoride diethyl etherate; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 3 h / 0 °C

10.2: pH 7

With trimethylsilyl trifluoromethanesulfonate; pyridine; 1H-imidazole; methanol; dmap; potassium osmate(VI); N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; tripotassium hexacyanoferrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; Methyltriphenylphosphonium bromide; sodium; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 1378358-27-0
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-β-D-manno-heptopyranose

: 1378358-25-8
1-deoxy-1-allyl-6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-manno-heptopyranose

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1H-imidazole / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; methanol / 1.66 h / 0 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / water; tetrahydrofuran / 2 h / Inert atmosphere

4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -70 °C / Inert atmosphere

4.2: 0.25 h

5.1: Methyltriphenylphosphonium bromide; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

6.1: potassium carbonate; potassium osmate(VI); tripotassium hexacyanoferrate / toluene; water; tert-butyl alcohol / 96 h / 0 °C

7.1: dmap; pyridine / 20 °C

8.1: N-Bromosuccinimide / acetonitrile / 6 h / -15 °C

8.2: 6 h / 20 °C

9.1: boron trifluoride diethyl etherate; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 3 h / 0 °C

9.2: pH 7

With trimethylsilyl trifluoromethanesulfonate; pyridine; 1H-imidazole; dmap; potassium osmate(VI); N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; tripotassium hexacyanoferrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; Methyltriphenylphosphonium bromide; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;