N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE

Base Information

• Chemical Name: N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE
• CAS No.: 207516-23-2
• Molecular Formula: C26H49NO4
• Molecular Weight: 439.679
• Mol file: 207516-23-2.mol

Synonyms:N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE;(4S,5R)-4-(HydroxyMethyl)-2,2-diMethyl-5-(1E)-1-pentadecen-1-yl-3-oxazolidinecarboxylic Acid 1,1-DiMethylethyl Ester

Chemical Property of N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 513.443°C at 760 mmHg
• PKA: 14.54±0.10(Predicted)
• Flash Point: 264.321°C
• PSA: 59.00000
• Density: 0.979g/cm³
• LogP: 6.91450
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-D-erythro-sphingosine-2,3-N,O-acetonide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A protected Sphingosine

Technology Process of N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE

There total 8 articles about N-BOC-D-ERYTHRO-SPHINGOSINE-2,3-N,O-ACETONIDE 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: 88.0%

(4S,5R)-4-Benzoyloxymethyl-2,2-dimethyl-5-((E)-pentadec-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester → tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate (207516-23-2)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1055/s-0029-1217956

Reference yield:

N-tert-butyloxycarbonylsphingosine (116467-63-1) + 2,2-dimethoxy-propane (77-76-9) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate (207516-23-2)

Guidance literature:

N-tert-butyloxycarbonylsphingosine; tert-butylchlorodiphenylsilane; With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h;

2,2-dimethoxy-propane; toluene-4-sulfonic acid; In benzene; for 0.5h; Reflux;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

Reference yield:

C42H67NO4Si (263543-27-7) → tert-butyl (4S,5R,1'E)-4-(hydroxymethyl)-2,2-dimethyl-5-(pentadec-1'-enyl)-oxazolidine-3-carboxylate (207516-23-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/jo902076w

upstream raw materials:

di-tert-butyl dicarbonate

N-tert-butyloxycarbonylsphingosine

Benzoic acid (E)-(2S,3R)-2-tert-butoxycarbonylamino-3-hydroxy-octadec-4-enyl ester

C₄₂H₆₇NO₄Si

Downstream raw materials:

C₆₀H₇₅NO₁₃

C₆₀H₇₅NO₁₃

(4S,5R,1''E)-tert-butyl-4-((((4'-bromo-5'-methoxy-2'-nitrophenyI)(phenyl)methoxy)(methoxy)phosphoryloxy)methyI)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate

tert-butyl (4S,5R,1''E)-4-((((4'-bromo-5'-hydroxy-2'-nitrophenyl)(phenyl)methoxy)(hydroxy)phosphoryloxy)methyl)-2,2-dimethyl-5-(pentadec-1''-enyl)oxazolidine-3-carboxylate

Refernces

• 1、 Michieletti, Mario,Sillani, Laura,Panza, Luigi. "A properly protected sphingosine acceptor for helferich glycosylation". scheme or table. p. 2609 - 2612. Retrieved 2010/02/28.
• 2、 Qiao, Lixin,Kozikowski, Alan P.,Olivera, Ana,Spiegel, Sarah. "Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP". . p. 711 - 714. Retrieved 2007/10/03.