2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

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Chemical Name:2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone
CAS No.:1378358-44-1
Molecular Formula:C₄₉H₄₉O₁₀P
Molecular Weight:828.896
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

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Chemical Property of 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

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Technology Process of 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

There total 12 articles about 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone 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: 61.0%

: 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranoside

: 1378358-44-1
2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

Guidance literature:: 2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-heptopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve ?;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 4h;

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

: 1378358-44-1
2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

Guidance literature:: Multi-step reaction with 12 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: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C

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

8.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

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

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

12.2: 4 h / 20 °C

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

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

: 1378358-44-1
2,3,4,6-tetra-O-benzyl-7-(dibenzyloxyphosphoryl)-D-glycero-D-manno-hepto-1,5-pyranone

Guidance literature:: Multi-step reaction with 13 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: 1H-imidazole / tetrahydrofuran / 16 h / 20 °C

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

9.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

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

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

13.2: 4 h / 20 °C

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