1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

Base Information

Chemical Name:1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose
CAS No.:1378358-48-5
Molecular Formula:C₅₂H₅₅O₁₁P
Molecular Weight:886.976
Hs Code.:

Synonyms:1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

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Chemical Property of 1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

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Technology Process of 1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

There total 19 articles about 1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-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: 82.0%

: 1378358-47-4
1-C-Hydroxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

: 108-24-7
acetic anhydride

: 1378358-48-5
1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

Guidance literature:: 1-C-Hydroxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose; acetic anhydride; With pyridine; dmap; at 20 ℃;

With triethylsilane; boron trifluoride-tetrahydrofuran complex; at 0 - 20 ℃; for 3h;

Reference yield:

: 100-39-0
benzyl bromide

: 1378358-48-5
1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; hexane; mineral oil / 0.33 h / 0 °C

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C

3.1: triethylamine; diethylazodicarboxylate / toluene; tetrahydrofuran / 24 h / 20 °C

4.1: N-Bromosuccinimide; water / acetone / 4 h / 0 °C

5.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve ?

5.2: 4 h / 20 °C

6.1: dimethyltitanocene / toluene / 2 h / 20 - 70 °C

7.1: potassium carbonate; potassium osmate(VI); tripotassium hexacyanoferrate / toluene; water; tert-butyl alcohol

8.1: dmap; pyridine / 20 °C

8.2: 3 h / 0 - 20 °C

With pyridine; dmap; potassium osmate(VI); N-Bromosuccinimide; tripotassium hexacyanoferrate; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; triethylamine; diethylazodicarboxylate; dimethyltitanocene; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol;

Reference yield:

: 7296-15-3
alpha-D-mannopyranoside

: 1378358-48-5
1-deoxy-1-β-C-acetoxymethylene 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranose

Guidance literature:: Multi-step reaction with 18 steps

1.1: pyridine / water / 15 h / 0 - 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 15.75 h / 20 °C / Inert atmosphere

3.1: sodium; methanol / 2 h / Inert atmosphere

3.2: IR-120 (Amberlite H form)

4.1: 1H-imidazole / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere

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

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

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

7.2: 0.25 h

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

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

10.1: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C

11.1: sodium hydride / N,N-dimethyl-formamide; hexane; mineral oil / 0.33 h / 0 °C

11.2: 3 h / 0 - 20 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 20 °C

13.1: triethylamine; diethylazodicarboxylate / toluene; tetrahydrofuran / 24 h / 20 °C

14.1: N-Bromosuccinimide; water / acetone / 4 h / 0 °C

15.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve ?

15.2: 4 h / 20 °C

16.1: dimethyltitanocene / toluene / 2 h / 20 - 70 °C

17.1: potassium carbonate; potassium osmate(VI); tripotassium hexacyanoferrate / toluene; water; tert-butyl alcohol

18.1: dmap; pyridine / 20 °C

18.2: 3 h / 0 - 20 °C

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