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Merck
CN

331813

(2S,3R)-(+)-N-Boc-6-氧代-2,3-二苯基吗啉

99%

别名:

(2S,3R)-(+)-6-氧代-2,3-二苯基-4-吗啉羧酸叔丁酯

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关于此项目

经验公式（希尔记法）:
C21H23NO4
化学文摘社编号:
112741-50-1
分子量:
353.41
MDL编号:
MFCD00074953
UNSPSC代码:
12352005
PubChem化学物质编号:
24860000
NACRES:
NA.22

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方案

99%

表单

solid

旋光性

[α]20/D +86°, c = 5.5 in methylene chloride

光学纯度

ee: 99% (HPLC)

mp

206 °C (dec.) (lit.)

官能团

ester
phenyl

储存温度

2-8°C

SMILES字符串

CC(C)(C)OC(=O)N1CC(=O)O[C@H]([C@H]1c2ccccc2)c3ccccc3

InChI

1S/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3/t18-,19+/m1/s1

InChI key

MRUKRSQUUNYOFK-MOPGFXCFSA-N

应用

(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine (Williams chiral auxiliary) can be used as a reactant:
  • In the asymmetric synthesis of cylindrospermopsin and related alkaloids via an intramolecular 1,3-dipolar cycloaddition reaction.
  • To synthesize boc-3-(1-methylcyclopropyl)-D-alanine, which is used as an intermediate to prepare 4-fluoroproline-based analogs as potent tripeptide thrombin inhibitors.
  • In the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin by intramolecular 1,3-dipolar cycloaddition and nitroaldol reaction.
  • To prepare differentially functionalized diaminoglutamic acids via radical reaction of selenide with methyl 2-acetamidoacrylate.

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315,H319,H335

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCS5649
MKBQ9762V
MKBD0043
MKBB3468
02007KJ

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Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability
Staas DD, et al.
Bioorganic & Medicinal Chemistry, 14(20), 6900-6916 (2006)
A Concise Asymmetric Synthesis of the Marine Hepatotoxin 7-Epicylindrospermopsin
Looper RE and Williams RM
Angewandte Chemie (International ed. in English), 43(22), 2930-2933 (2004)
Radical reaction of Williams? glycinate auxiliaries with α-amidoacrylates: synthesis of orthogonally functionalized (2R, 4R)-and (2R, 4S)-diaminoglutamic acids
Kabat MM
Tetrahedron Letters, 42(42), 7521-7524 (2001)
Syntheses of the cylindrospermopsin alkaloids
Looper RE, et al.
Tetrahedron, 62(18), 4549-4562 (2006)

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