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Quality Control of H-D-Leu-OBzl·TosOH Purity: 97% SDS Specification

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Product Details of H-D-Leu-OBzl·TosOH

CAS No. :	17664-93-6
Formula :	C₂₀H₂₇NO₅S
M.W :	393.50
SMILES Code :	CC(C)C[C@@H](N)C(OCC1=CC=CC=C1)=O.O=S(C2=CC=C(C)C=C2)(O)=O
MDL No. :	MFCD00066116
InChI Key :	QTQGHKVYLQBJLO-UTONKHPSSA-N
Pubchem ID :	44629929

Safety of H-D-Leu-OBzl·TosOH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of H-D-Leu-OBzl·TosOH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 17664-93-6 ]

[ 17664-93-6 ] Synthesis Path-Downstream 1~41

1
[ 2130-96-3 ]
[ 17664-93-6 ]
[ 66959-93-1 ]

References: [1]Patent: DE2741393,1978, .
Chem.Abstr.,1978,vol. 89.

2
[ 59969-65-2 ]
[ 17664-93-6 ]
[ 62058-27-9 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 510 - 515.

3
[ 62023-58-9 ]
[ 17664-93-6 ]
[ 62058-31-5 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 510 - 515.

4
[ 17664-93-6 ]
[ 62023-60-3 ]
(R)-2-((2R,3S)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 510 - 515.

5
[ 17664-93-6 ]
[ 62023-59-0 ]
[ 62058-29-1 ]

References: [1]Journal of Medicinal Chemistry,1977,vol. 20,p. 510 - 515.

6
[ 5292-43-3 ]
[ 17664-93-6 ]
(R)-2-(tert-Butoxycarbonylmethyl-amino)-4-methyl-pentanoic acid benzyl ester; compound with toluene-4-sulfonic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

7
[ 37553-65-4 ]
[ 17664-93-6 ]
(R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1859 - 1863.

8
[ 13748-90-8 ]
[ 17664-93-6 ]
[ 184034-25-1 ]

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 1657 - 1666.

9
[ 3303-84-2 ]
[ 17664-93-6 ]
[ 223270-78-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

10
[ 17664-93-6 ]
[ 124072-61-3 ]
[ 223270-79-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

Yield	Reaction Conditions	Operation in experiment
99%		D-Leucine O-benzyl ester Tosylate salt To benzyl alcohol (8.2 g) dissolved in benzene (30 mL) was added D-leucine (5.0 g) and p-toluenesulfonic acid monohydrate (8.0 g). The reaction was warmed to reflux with removal of water overnight. Once TLC indicated consumption of starting material, the reaction was cooled, and the resulting solid was filtered and washed with EtOAc to give the title compound as a white powder (14.26 g, 99%).
73%		A. Benzyl D-Leucinate p-Toluenesulfonate This compound was prepared in a manner corresponding precisely to that described in Part A of Example 1 for preparation of the D-alinate compound. Yield, 73%, m.p. 155-156 C. Analysis, calculated for C20 H27 NO5 S (393.50): C, 61.05; H, 6.92; N, 3.56. Found: C, 61.17; H, 6.68; N, 3.81.

12
[ 98-01-1 ]
[ 17664-93-6 ]
(R)-2-[1-Furan-2-yl-meth-(E)-ylidene]-amino}-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

13
[ 17664-93-6 ]
[ 100-52-7 ]
(R)-4-Methyl-2-[1-phenyl-meth-(E)-ylidene]-amino}-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

14
[ 17664-93-6 ]
[ 144085-23-4 ]
[ 387823-63-4 ]

References: [1]Tetrahedron,2004,vol. 60,p. 5177 - 5183.

15
[ 17664-93-6 ]
[ 731807-68-4 ]
(R)-2-[2-((R)-1-Benzyloxycarbonyl-3-methyl-butylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester [ No CAS ]

References: [1]Tetrahedron,2004,vol. 60,p. 5177 - 5183.

16
[ 17664-93-6 ]
(5R)-7-[(1R)-1-benzyloxycarbonyl-3-methylbutyl]-1-(tert-butoxycarbonyl)-6-oxo-1,7-diazaspiro[4.4]nonane [ No CAS ]

References: [1]Tetrahedron,2004,vol. 60,p. 5177 - 5183.

17
[ 17664-93-6 ]
(R)-2-[(Dimethoxy-phosphoryl)-phenyl-methyl]-amino}-4-methyl-pentanoic acid [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

18
[ 17664-93-6 ]
(R)-2-[(Dimethoxy-phosphoryl)-furan-2-yl-methyl]-amino}-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

19
[ 17664-93-6 ]
[ 282725-28-4 ]

References: [1]Synlett,2000,p. 698 - 700.

20
[ 17664-93-6 ]
(R)-2-[(Diethoxy-phosphoryl)-phenyl-methyl]-amino}-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

21
[ 17664-93-6 ]
(R)-2-[(Diphenyl-phosphinoyl)-phenyl-methyl]-amino}-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

22
[ 17664-93-6 ]
(R)-2-[(Diphenyl-phosphinoyl)-furan-2-yl-methyl]-amino}-4-methyl-pentanoic acid benzyl ester [ No CAS ]

References: [1]Synlett,2000,p. 698 - 700.

23
[ 17664-93-6 ]
[ 223270-81-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

24
[ 17664-93-6 ]
[ 223270-82-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

25
[ 17664-93-6 ]
(3S,6R,13S,16S)-13-Benzyl-3,6,16-triisobutyl-11,14-dimethyl-1-oxa-4,7,11,14-tetraaza-cyclohexadecane-2,5,8,12,15-pentaone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

26
[ 17664-93-6 ]
(3S,6R,13S,16S)-13-Benzyl-3,6,16-triisobutyl-14-methyl-1-oxa-4,7,11,14-tetraaza-cyclohexadecane-2,5,8,12,15-pentaone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

27
[ 17664-93-6 ]
[ 223270-90-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

28
[ 17664-93-6 ]
[ 223270-91-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

29
[ 17664-93-6 ]
[ 223270-88-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

30
[ 17664-93-6 ]
[ 223270-87-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

31
[ 17664-93-6 ]
[ 223270-85-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

32
[ 17664-93-6 ]
[ 223270-84-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 563 - 568.

33
[ 17664-93-6 ]
[ 128684-59-3 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

34
[ 17664-93-6 ]
[ 128708-18-9 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

35
[ 17664-93-6 ]
[ 128708-19-0 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

36
[ 17664-93-6 ]
[ 128684-65-1 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

37
[ 17664-93-6 ]
[ 128684-66-2 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

38
[ 17664-93-6 ]
D-Phe-Lys(COCH₂-D-Leu-OH)-D-Trp-NH(CH₂)2CHMe₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

39
[ 17664-93-6 ]
(R)-2-[((R)-1-{(S)-5-Amino-1-[(R)-2-(1H-indol-3-yl)-1-(3-methyl-butylcarbamoyl)-ethylcarbamoyl]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-methyl]-amino}-4-methyl-pentanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2560 - 2568.

40
[ 17664-93-6 ]
[ 46741-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water;	Preparation of 3-[(1R)-1-(benzyloxycarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acid (Compound HI); D-Leucine benzylester p-tosylate (2.5 g, 6.3 mmol) was treated with an aqueous solution of K2CO3 (30 mL). The mixture was extracted with EtOAc (3×30 mL). The organic extracts were separated, combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To a solution of D-Leucine benzylester (6.3 mmol) in acetonitrile (9 mL) and MeOH (3 mL) was added 1,3-propane sultone (691 mg, 5.7 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid material was filtered and washed with aconitrile (2×20 mL). The solid was dissolved in 20% water/EtOH (75 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and dried in vacuo, affording the title compound (960 mg, 49%). 1H NMR (D2O, 500 MHz) delta ppm 7.52 (m, 5H), 5.41 (d, 1H, J=12.2 Hz), 5.35 (d, 1H, J=12.2 Hz), 4.16 (m, 1H), 3.22 (m, 2H), 2.97 (t, 2H, J=6.8 Hz), 2.16 (m, 2H), 1.88 (m, 1H), 1.79 (m, 1H), 1.76 (m, 1H), 0.94 (d, 6H, J=3.9 Hz). 13C (DMSO, 125 MHz) delta ppm 169.60, 135.62, 129.24, 129.21, 129.11, 68.08, 58.09, 49.87, 46.48, 24.77, 23.50, 22.50, 22.04. [alpha]D=-2.1 (c=0.00095 in water), ES-MS 344 (M+1).

References: [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 141.

41
(2S,3R)-3-N-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoyl-(S)-leucine [ No CAS ]
[ 17664-93-6 ]
(2S,3)-3-amino-2-hydroxy-4-phenylbutanoyl-(S)-leucyl-(R)-leucine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 14 Synthesis of (2S,3)-3-amino-2-hydroxy-4-phenylbutanoyl-(S)-leucyl-(R)-leucine (2S,3R)-3-N-Benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoyl-(S)-leucine (1.11 g) was reacted with 983.3 mg of <strong>[17664-93-6](R)-leucine benzylester p-toluenesulfonate</strong> and the resulting condensation product was isolated in the same manner as in the step (a) of Example 12 to give 1.39 g of the 3-N-benzyloxycarbonyl-protected derivative of (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-(S)-leucyl-(R)-leucine as a powder. This protected product showed a value of m/e 646 in the analysis of mass spectrometry.

References: [1]Patent: US4370318,1983,A .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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P321
P322
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P342	If experiencing respiratory symptoms:
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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CAS No.: 17664-93-6

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CAS No.: 17664-93-6

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Product Details of H-D-Leu-OBzl·TosOH

Safety of H-D-Leu-OBzl·TosOH

Application In Synthesis of H-D-Leu-OBzl·TosOH

[ 17664-93-6 ] Synthesis Path-Downstream 1~41

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