(4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

Base Information

• Chemical Name: (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline
• CAS No.: 78249-25-9
• Molecular Formula: C₃₇H₄₇NO₆
• Molecular Weight: 601.783
• Mol file: 78249-25-9.mol

Synonyms:(4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

Chemical Property of (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

There total 10 articles about (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline 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:

5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose (62853-46-7) → (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline (78249-25-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / 1.) NaH / tetrahydrofuran / 1.) reflux, 1h, 2.) 25 deg C, 17.5h

2: 4percent H₂SO₄ aq / dioxane / 2 h / Heating

3: NaBH₄ / ethanol / 72 h / Ambient temperature

4: H₂SO₄ aq / CH₂Cl₂ / 46 h / molecular sieves

5: 90 percent / CrO₃, (CH₃CO)2O, C₅H₅N / CH₂Cl₂ / 0.33 h

6: NaH / 1.) 1,2-dimethoxyethane, room temp., 70 min, 2.) dimethoxyethane, 0 deg C, 4h

7: 1.) Li

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; acetic anhydride; lithium; sodium hydride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1021/jo00332a023

Reference yield:

5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-alpha-D-xylo-hex-5-enofuranose (19877-09-9) → (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline (78249-25-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) 2-methyl-2-butene, (CH₃)2S*BH₃, 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, 0-25 deg C, 18.5h, 2.) 0-25 deg C, 2.0h

2: 93 percent / 1.) NaH / tetrahydrofuran / 1.) reflux, 1h, 2.) 25 deg C, 17.5h

3: 4percent H₂SO₄ aq / dioxane / 2 h / Heating

4: NaBH₄ / ethanol / 72 h / Ambient temperature

5: H₂SO₄ aq / CH₂Cl₂ / 46 h / molecular sieves

6: 90 percent / CrO₃, (CH₃CO)2O, C₅H₅N / CH₂Cl₂ / 0.33 h

7: NaH / 1.) 1,2-dimethoxyethane, room temp., 70 min, 2.) dimethoxyethane, 0 deg C, 4h

8: 1.) Li

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; acetic anhydride; lithium; sodium hydride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;

DOI:10.1021/jo00332a023

Reference yield:

6-O-Benzyl-5-deoxy-3-O-methyl-D-glucofuranose (78249-06-6,78249-07-7) → (4S,5S)-2-<(2R,3S,4R,5S)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-(2-methylpropyl)heptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline (78249-25-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄ / ethanol / 72 h / Ambient temperature

2: H₂SO₄ aq / CH₂Cl₂ / 46 h / molecular sieves

3: 90 percent / CrO₃, (CH₃CO)2O, C₅H₅N / CH₂Cl₂ / 0.33 h

4: NaH / 1.) 1,2-dimethoxyethane, room temp., 70 min, 2.) dimethoxyethane, 0 deg C, 4h

5: 1.) Li

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; acetic anhydride; lithium; sodium hydride; In ethanol; dichloromethane;

DOI:10.1021/jo00332a023

upstream raw materials:

Isobutyl bromide

(+)-(5S,4S)-2-<(3S,4R,5S)-7-(Benzyloxy)-5,3-(benzylidenedioxy)-4-methoxy-(E)-1-heptenyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

(4S,5S)-(-)-4,5-dihydro-4-methoxymethyl-2-methyl-5-phenyloxazole

5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose

Downstream raw materials:

(4R,5S)-4-(2-Methylpropyl)-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

(4S,5S)-5-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methoxy-butyl)-4-isobutyl-dihydro-furan-2-one