(4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

Base Information

• Chemical Name: (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone
• CAS No.: 124379-81-3
• Molecular Formula: C₂₉H₄₁NO₇
• Molecular Weight: 515.647
• Mol file: 124379-81-3.mol

Synonyms:(4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

Chemical Property of (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

There total 3 articles about (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-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:

(2S,3R,4S,5R)-2,4,6-trimethyl-3,5-[(bis-dimethylmethylene)dioxy]hept-6-enal (124356-89-4) + (S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione (101712-01-0) → (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone (124379-81-3)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine; Yield given. Multistep reaction; 1.) -20 deg C, 1 h, CH₂Cl₂, 2.) -78 deg C, 30 min;

DOI:10.1021/ja00158a056

Reference yield:

<4R,5S,6S,(1R)>-4-(1-methylethenyl)-6-(2-hydroxy-1-methylethyl)-2,2,5-trimethyl-1,3-dioxane (124356-94-1) → (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone (124379-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₃*pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / -5 °C

2: 1) Sn(OTf)2, Et₃N / 1) CH₂Cl₂, -20 deg C, 1 h, 2) -78 deg C, 30 min

With tin(II) trifluoromethanesulfonate; pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00305a006

Reference yield:

<3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone (124356-84-9) → (4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-hydroxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone (124379-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / NaBH(OAc)3, HOAc / 1 h / 25 °C

2: Dowex-50 / CH₂Cl₂ / 1 h / 25 °C

3: LiAlH₄ / tetrahydrofuran / 1 h / -78 °C

4: SO₃*pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / -5 °C

5: 1) Sn(OTf)2, Et₃N / 1) CH₂Cl₂, -20 deg C, 1 h, 2) -78 deg C, 30 min

With lithium aluminium tetrahydride; tin(II) trifluoromethanesulfonate; pyridine-SO₃ complex; Dowex-50; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00305a006

upstream raw materials:

(2S,3R,4S,5R)-2,4,6-trimethyl-3,5-[(bis-dimethylmethylene)dioxy]hept-6-enal

(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

<4R,5S,6S,(1R)>-4-(1-methylethenyl)-6-(2-hydroxy-1-methylethyl)-2,2,5-trimethyl-1,3-dioxane

<3(2S,4R,5R),4S>-3-(1,3-dioxo-5-hydroxy-2,4,6-trimethyl-6-heptenyl)-4-(phenylmethyl)-2-oxazolidinone

Downstream raw materials:

(4S)-4-benzyl-3-<(2S,4R,5S,6R)-5-methoxy-6-<(4S,5R,6R)-6-isopropenyl-2,2,5-trimethyl-1,3-dioxan-4-yl>-2,4-dimethyl-3-oxoheptanoyl>-2-oxazolidinone

(S)-2-{(4R,5S,6S)-6-[(1R,2S,3R,5S)-6-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methoxy-1,3,5-trimethyl-4,6-dioxo-hexyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

(2S,4R,5S,6R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-6-[(4S,5R,6S)-6-((R)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-2,4-dimethyl-heptane-1,3-dione

(2S,4R,5S,6R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-6-[(4S,5R,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methoxy-2,4-dimethyl-heptane-1,3-dione