(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol
CAS No.:1291093-88-3
Molecular Formula:C₂₉H₃₂ClNO₇
Molecular Weight:542.029
Hs Code.:

Synonyms:(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

There total 8 articles about (2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-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:

: 67-56-1
methanol

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

: 1291093-87-2
4-benzyl-6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine

: 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

: 1291093-88-3
(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

Guidance literature:: 4-benzyl-6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine; 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:

: 67-56-1
methanol

: 1291093-87-2
4-benzyl-6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine

: 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

: 1291093-88-3
(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

Guidance literature:: 4-benzyl-6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine; With n-butyllithium; In tetrahydrofuran; hexanes; toluene; at -78 ℃; for 1h;

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

methanol; With methanesulfonic acid; In tetrahydrofuran; hexanes; toluene; at 20 ℃; for 12h; Product distribution / selectivity;

Reference yield:

: 5466-88-6
3,4-dihydro-3-oxo-2H-1,4-benzoxazine

: 1291093-88-3
(2S,3R,4S,5S,6R)-2-[3-(4-benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-4-chloro-phenyl]-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: dichloromethane / Cooling with ice

3.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C

4.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile; 1,2-dichloro-ethane / 4 h / 50 °C

5.1: sodium tetrahydroborate / ethanol

6.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 50 °C

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

7.2: -78 °C

With triethylsilane; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; boron trifluoride diethyl etherate; potassium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;