(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

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Chemical Name:(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide
CAS No.:711238-16-3
Molecular Formula:C₂₄H₃₁NO₇
Molecular Weight:445.513
Hs Code.:

Synonyms:(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

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Chemical Property of (2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

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Technology Process of (2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

There total 5 articles about (2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide 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: 43.0%

: 20989-17-7
(2S)-2-phenylglycinol

: 711238-11-8
(2R,3S,5R,6R)-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-carboxylic acid

: 711238-16-3
(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

Guidance literature:: In xylene; for 17h; Heating;
DOI:10.1002/ejoc.200300750

Reference yield:

: 439917-06-3
(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-dicarboxylic acid monomethyl ester

: 711238-16-3
(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 77 percent / 4-dimethylaminopyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 4 h / 0 °C

2.1: 82 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

3.1: 68 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -60 - -50 °C

5.1: 72 percent / hexane; tetrahydrofuran / 1.33 h / Heating

6.1: HCl / tetrahydrofuran; H₂O / 0.67 h / 0 °C / pH 1

6.2: LiOH / tetrahydrofuran; H₂O / 4.66 h / pH 11 / Heating

7.1: 43 percent / xylene / 17 h / Heating

With hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; xylene; 4.1: Swern oxidation / 5.1: Grignard reaction;
DOI:10.1002/ejoc.200300750

Reference yield:

: 711237-97-7
[(2S,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1,4-dioxan-2-yl]methanol

: 711238-16-3
(2R,3S,5R,6R)-N-[(S)-2-hydroxy-1-phenylethyl]-3-(hydroxyphenylmethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -60 - -50 °C

2.1: 72 percent / hexane; tetrahydrofuran / 1.33 h / Heating

3.1: HCl / tetrahydrofuran; H₂O / 0.67 h / 0 °C / pH 1

3.2: LiOH / tetrahydrofuran; H₂O / 4.66 h / pH 11 / Heating

4.1: 43 percent / xylene / 17 h / Heating

With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; xylene; 1.1: Swern oxidation / 2.1: Grignard reaction;
DOI:10.1002/ejoc.200300750