[glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine

Base Information

• Chemical Name: [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine
• CAS No.: 299172-60-4
• Molecular Formula: C₄₁H₅₈F₃NO₁₃
• Molecular Weight: 835.84
• Mol file: 299172-60-4.mol

Synonyms:

Chemical Property of [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine

There total 11 articles about [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine 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: 27.0%

(2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-4-sphingenine (18459-13-7) + [glucose-U-(13)C]-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (299172-54-6) → Benzoic acid (E)-(R)-1-[(S)-2-acetoxy-1-(2,2,2-trifluoro-acetylamino)-ethyl]-hexadec-2-enyl ester + [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine (299172-60-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 10h;

DOI:10.1039/b002104k

Reference yield:

(4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester (115464-01-2) → [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine (299172-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 35 percent / Red-Al / toluene; diethyl ether / 22 h / 20 °C

2: 53 percent / pyridine; DMAP / 2 h

3: 39 percent / trifluoroacetic acid / 3 h

4: 54 percent / pyridine / 2 h / 55 °C

5: 27 percent / 4 Angstroem molecular sieves; BF₃*OEt / CH₂Cl₂ / 10 h / 20 °C

With pyridine; dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; In diethyl ether; dichloromethane; toluene; 2: Mitsunobu reaction;

DOI:10.1039/b002104k

Reference yield:

N-tert-butyloxycarbonylsphingosine (116467-63-1) → [glucose-U-(13)C]-3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-D-erythro-sphingosine (299172-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / pyridine; DMAP / CH₂Cl₂ / 26.5 h / 20 - 75 °C

2: 98 percent / pyridine; DMAP / 2 h

3: 57 percent / acetyl chloride / methanol / 1.5 h

4: 54 percent / pyridine / 2 h / 55 °C

5: 27 percent / 4 Angstroem molecular sieves; BF₃*OEt / CH₂Cl₂ / 10 h / 20 °C

With pyridine; dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; acetyl chloride; In methanol; dichloromethane;

DOI:10.1039/b002104k

upstream raw materials:

(2S,3R,4E)-3-O-benzoyl-N-trifluoroacetyl-4-sphingenine

[glucose-U-(13)C]-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate

(4S,1'R)-4-(1'-Hydroxy-2'-hexadecinyl)-2,2-dimethyl-3-oxazolidincarbonsaeure-tert-butylester

N-tert-butyloxycarbonylsphingosine

Downstream raw materials:

[glucose-(13)C6]-1-O-(β-D-glucopyranosyl)-D-erythro-sphingosine