(2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol

Base Information

• Chemical Name: (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol
• CAS No.: 162119-30-4
• Molecular Formula: C₃₁H₅₂N₄O₉
• Molecular Weight: 624.775
• Mol file: 162119-30-4.mol

Synonyms:

Chemical Property of (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol

There total 11 articles about (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol 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:

(1S,2R,6R)-2-hydroxymethyl-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-4-ene (157609-10-4) → (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol (162119-30-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / phosphate buffer (1M Na₂HPO₄/1M NaH₂PO₄ 1:1), m-chloroperbenzoic acid / 1,2-dichloro-ethane / 6 h / Ambient temperature

2: 1.) sodium azide; 2.) pyridine / 1.) DMF, 24 h, 90 deg C

3: 0.1M sodium methoxide / methanol / 1 h / Ambient temperature

4: H₂ / Raney nickel T-4 / ethanol / 4 h / Ambient temperature

5: 77 percent / propan-2-ol / 48 h / 120 °C

6: 1M tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

7: aq. 80percent acetic acid / 1 h / 90 °C

With pyridine; sodium azide; phosphate buffer (1M Na₂HPO₄/1M NaH₂PO₄; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; 3-chloro-benzenecarboperoxoic acid; Raney nickel T-4; In tetrahydrofuran; methanol; ethanol; 1,2-dichloro-ethane; isopropyl alcohol;

Reference yield:

1,2-anhydro-3,4-O-isopropylidene-5a-carba-α-D-galactopyranose (162020-08-8) → (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol (162119-30-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium azide; 2.) pyridine / 1.) DMF, 24 h, 90 deg C

2: 0.1M sodium methoxide / methanol / 1 h / Ambient temperature

3: H₂ / Raney nickel T-4 / ethanol / 4 h / Ambient temperature

4: 77 percent / propan-2-ol / 48 h / 120 °C

5: 1M tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

6: aq. 80percent acetic acid / 1 h / 90 °C

With pyridine; sodium azide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; Raney nickel T-4; In tetrahydrofuran; methanol; ethanol; isopropyl alcohol;

Reference yield:

(3aR,4S,5R,7R,7aS)-5-Azido-7-hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol → (2S,3R,4E)-1-(5a-carba-β-D-galactopyranosylamino)-2-(2,4-dinitrophenyl)amino-4-octadecen-3-ol (162119-30-4)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Raney nickel T-4 / ethanol / 4 h / Ambient temperature

2: 77 percent / propan-2-ol / 48 h / 120 °C

3: 1M tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: aq. 80percent acetic acid / 1 h / 90 °C

With tetrabutyl ammonium fluoride; hydrogen; acetic acid; Raney nickel T-4; In tetrahydrofuran; ethanol; isopropyl alcohol;

upstream raw materials:

2-azido-sphingosine

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol

2,4-Dinitrofluorobenzene

(1S,2R,6R)-2-hydroxymethyl-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-4-ene

Refernces