(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Base Information

Chemical Name:(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone
CAS No.:186489-70-3
Molecular Formula:C₂₃H₃₃NO₆
Molecular Weight:419.518
Hs Code.:

Synonyms:(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

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Chemical Property of (4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

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Technology Process of (4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

There total 1 articles about (4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone 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:

: 186489-69-0
(R)-4-Benzyl-3-[(R)-2-((4S,5S,6R)-6-isopropenyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propionyl]-oxazolidin-2-one

: (4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1R)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

: 186489-70-3
(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

Guidance literature:: With dihydrogen peroxide; dimeric 9-borabicyclo[3.3.1]nonane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, a) 0 deg C, 4 h, b) RT, 13 h, 2.) THF, MeOH, 1 h;
DOI:10.1021/ja9806128

Reference yield:

: 186489-70-3
(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

: 186489-77-0
(R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2R,3S,4S,5S,6R,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2,4-dihydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) 0 deg C, 1 h

2: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

3: 95 percent / Zn(BH₄)2 / CH₂Cl₂; diethyl ether / 1 h / 0 °C

With zinc(II) tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja9806128

Reference yield:

: 186489-70-3
(4R)-4-benzyl-3-{(2R)-2-[(4S,5R,6S)-6-((1S)-2-hydroxy-1-methylethyl)-2,2,5-trimethyl-m-dioxan-4-yl]propionyl}-2-oxazolidinone

: 171005-61-1
(R)-4-Benzyl-3-((R)-2-{(4S,5R,6S)-6-[(1S,2S,3R,5R,6S,7R,8R)-8-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-1,3,5,7-tetramethyl-4-oxo-decyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) 0 deg C, 1 h

2: 83 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

With oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja9806128