2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

Base Information

Chemical Name:2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol
CAS No.:913537-24-3
Molecular Formula:C₂₂H₂₇BrO₉
Molecular Weight:515.355
Hs Code.:

Synonyms:2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

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Chemical Property of 2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

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Technology Process of 2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

There total 7 articles about 2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol 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: 97.0%

: 913537-23-2
2,6-anhydro-1-deoxy-1-[4-(methoxymethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-galo-heptitol

: 913537-24-3
2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

Guidance literature:: 2,6-anhydro-1-deoxy-1-[4-(methoxymethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-galo-heptitol; With hydrogen bromide; acetic acid; at 0 - 20 ℃; for 18.5h;

With water; sodium hydrogencarbonate; In dichloromethane;

Reference yield: 71.0%

: 2,6-anhydro-1-deoxy-1-[4-(methyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-gulo-heptitol

: 913537-24-3
2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

Guidance literature:: With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h; Inert atmosphere; Reflux;
DOI:10.1080/07328303.2016.1227831

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 913537-24-3
2,6-anhydro-1-deoxy-1-[4-(bromomethyl)phenyl]-3,4,5,7-tetra-O-acetyl-D-glycero-D-guloheptitol

Guidance literature:: Multi-step reaction with 6 steps

1.1: acetic anhydride; dimethyl sulfoxide / 20 °C / Inert atmosphere

2.1: toluene / 70 °C / Inert atmosphere

3.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 4.5 h / Inert atmosphere; Reflux

3.2: 18 h / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / dichloromethane; methanol / 20 °C / Inert atmosphere

5.1: pyridine; dmap / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

6.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / Inert atmosphere; Reflux

With pyridine; dmap; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; palladium 10% on activated carbon; hydrogen; acetic anhydride; dimethyl sulfoxide; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: |Swern Oxidation / 3.2: |Suzuki Coupling;
DOI:10.1080/07328303.2016.1227831