methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside
CAS No.:1520094-80-7
Molecular Formula:C₄₆H₆₆FO₁₄PSi₂
Molecular Weight:949.165
Hs Code.:

methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

Synonyms:methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

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Technology Process of methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

There total 8 articles about methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside 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%

: 1520094-78-3
methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-3-O-(4-oxopentanoyl)-6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-L-glycero-α-D-manno-heptopyranoside

: 1520094-80-7
methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With triethylamine tris(hydrogen fluoride); In dichloromethane; at 0 ℃; for 3.5h; regioselective reaction;
DOI:10.1021/jo402312x

Reference yield:

: 127642-33-5,686299-10-5
methyl L-glycero-α-D-manno-heptopyranoside

: 1520094-80-7
methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / -55 - 20 °C

2: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 20 °C

3: water / 1 h / 20 °C

4: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C

5: 1H-tetrazole / dichloromethane; acetonitrile / 0.17 h / 20 °C

6: 3-chloro-benzenecarboperoxoic acid / dichloromethane; acetonitrile / 1.25 h / -78 °C

7: triethylamine tris(hydrogen fluoride) / dichloromethane / 3.5 h / 0 °C

With 1H-imidazole; 1H-tetrazole; dmap; camphor-10-sulfonic acid; water; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo402312x

Reference yield:

: 1520094-68-1
methyl 6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-Lglycero-α-D-manno-heptopyranoside

: 1520094-80-7
methyl 2-O-benzoyl-4-O-dibenzyloxyphosphoryl-6-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-1-yl)-3-O-(4-oxopentanoyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 20 °C

2: water / 1 h / 20 °C

3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C

4: 1H-tetrazole / dichloromethane; acetonitrile / 0.17 h / 20 °C

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane; acetonitrile / 1.25 h / -78 °C

6: triethylamine tris(hydrogen fluoride) / dichloromethane / 3.5 h / 0 °C

With 1H-tetrazole; dmap; camphor-10-sulfonic acid; water; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;
DOI:10.1021/jo402312x