(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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Chemical Name:(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
CAS No.:1291094-66-0
Molecular Formula:C₂₂H₂₅BrO₈
Molecular Weight:497.34
Hs Code.:

Synonyms:(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

There total 5 articles about (3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 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: 43.7%

: 67-56-1
methanol

: 1291094-65-9
6-[(2-bromo-5-iodophenyl)methyl]-2,3-dihydro-1,4-benzodioxin

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1291094-66-0
(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: 6-[(2-bromo-5-iodophenyl)methyl]-2,3-dihydro-1,4-benzodioxin; With n-butyllithium; In tetrahydrofuran; hexane; toluene; for 1h; Cooling with ice;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 2h;

methanol; With methanesulfonic acid; In tetrahydrofuran; hexane; toluene; at 20 ℃;

Reference yield:

: 67-56-1
methanol

: 75-75-2,98527-29-8
methanesulfonic acid

: 1291094-65-9
6-[(2-bromo-5-iodophenyl)methyl]-2,3-dihydro-1,4-benzodioxin

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1291094-66-0
(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: 6-[(2-bromo-5-iodophenyl)methyl]-2,3-dihydro-1,4-benzodioxin; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -78 ℃;

methanol; methanesulfonic acid;

Reference yield:

: 25252-00-0
2-bromo-5-iodobenzoic acid

: 1291094-66-0
(3R,4S,5S,6R)-2-(4-bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)meth yl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C

2.1: dichloromethane / 0 - 20 °C

3.1: trifluoroacetic acid; boron trifluoride diethyl etherate; trifluorormethanesulfonic acid / 0.42 h / 20 °C

4.1: n-butyllithium / toluene; hexane; tetrahydrofuran / -78 °C

4.2: -78 °C

With n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; trifluoroacetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; toluene;