N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine

Base Information

• Chemical Name: N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine
• CAS No.: 175696-50-1
• Molecular Formula: C23H47NO5
• Molecular Weight: 417.63
• Mol file: 175696-50-1.mol

Synonyms:N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine;

Chemical Property of N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine

Chemical Property:

• PSA: 99.02000
• LogP: 5.07590
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane

Purity/Quality:

N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected D-ribo-Phytosphingosine (P398990). A natural compound with antifungal activity.

Technology Process of N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine

There total 40 articles about N-tert-Butyloxycarbonyl-D-ribo-phytosphingosine 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: 98.0%

D-ribo-phytosphingosine (554-62-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate (175696-50-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1177/1747519820961018

Reference yield: 95.0%

(2S,3S,4R)-2-[(R)-1-phenylethylamino]octadecane-1,3,4-triol (925222-46-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate (175696-50-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 20 ℃; under 5171.48 Torr;

DOI:10.1039/b612740a

Reference yield: 88.0%

(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate (124127-36-2) → tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate (175696-50-1)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 0 - 20 ℃;

DOI:10.1021/jo1005284

upstream raw materials:

(2R,3Z)-2-(tert-butoxycarbonyl)amino-3-octadecen-1-ol

D-ribo-phytosphingosine

di-tert-butyl dicarbonate

(2S,3S,4R)-2-[(R)-1-phenylethylamino]octadecane-1,3,4-triol

Downstream raw materials:

[(E)-(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-allyl]-carbamic acid tert-butyl ester

N-tert-butyloxycarbonylsphingosine

(2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

(2S,3S,4R)-1-O-(6-deoxy-6-acetamido-α-D-galactopyranosyl)-2-(N-nervonoylamino)-1,3,4-octadecanetriol

Refernces

• 1、 Lee, Sun-Hee,Park, Sun-Kyoung,Kim, Jeong-Mi,Kim, Myung-Hwa,Kim, Kwang-Hee,Chun, Kwang-Woo,Cho, Kyung-Hea,Youn, Ji-Youn,Namgoong, Sung Keon. "New synthetic thiocolchicine derivatives as low-toxic anticancer agents". . p. 582 - 589. Retrieved 2005.
• 2、 -. "4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO". Page/Page column 295. . Retrieved 2019/10/01.