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Quality Control of H-D-Ala-OBzl·TosOH Purity: 98% SDS Specification

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Product Details of H-D-Ala-OBzl·TosOH

CAS No. :	41036-32-2
Formula :	C₁₇H₂₁NO₅S
M.W :	351.42
SMILES Code :	O=S(C1=CC=C(C)C=C1)(O)=O.C[C@@H](N)C(OCC2=CC=CC=C2)=O
Synonyms :	H-D-Ala-OBzl.TosOH
MDL No. :	MFCD00039092
InChI Key :	NWOPHJSSBMABBD-DDWIOCJRSA-N
Pubchem ID :	2802425

Safety of H-D-Ala-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-Ala-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 [ 41036-32-2 ]

[ 41036-32-2 ] Synthesis Path-Downstream 1~35

1
[ 41036-32-2 ]
(S)-2-tert-Butoxycarbonylamino-heptanedioic acid 7-benzyl ester [ No CAS ]
[ 18814-51-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1976,vol. 49,p. 533 - 539.

2
[ 3262-72-4 ]
[ 41036-32-2 ]
[ 92261-75-1 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 5 - 14.

3
[ 1676-90-0 ]
[ 41036-32-2 ]
[ 92398-55-5 ]

References: [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1663 - 1668.

4
[ 41036-32-2 ]
[ 70642-87-4 ]
[ 96523-76-1 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 647 - 655.

5
[ 41036-32-2 ]
[ 55878-47-2 ]
[ 96523-81-8 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 647 - 655.

6
[ 41036-32-2 ]
Boc-D-Arg(NO₂) [ No CAS ]
[ 92261-84-2 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 5 - 14.

7
[ 41036-32-2 ]
[ 65717-64-8 ]
[ 96523-69-2 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 647 - 655.

8
[ 41036-32-2 ]
[ 3401-36-3 ]
[ 132343-11-4 ]

References: [1]Bulletin de la Societe Chimique de France,1969,p. 2743 - 2747.

9
[ 41036-32-2 ]
[ 49827-15-8 ]
[ 171557-07-6 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 6987 - 6997.

10
[ 41036-32-2 ]
C₉H₁₅BrO₄ [ No CAS ]
(2R)-2-(3-Bromo-2-methylpropionylamino)propionic acid benzyl ester [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 131 - 142.

12
[ 41036-32-2 ]
[ 100-52-7 ]
(R)-2-[1-Phenyl-meth-(E)-ylidene]-amino}-propionic acid benzyl ester [ No CAS ]

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

13
[ 41036-32-2 ]
[ 186753-98-0 ]
[ 263010-60-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 32 - 40.

14
[ 5068-28-0 ]
[ 41036-32-2 ]
Boc-Cys(SBn)-D-Ala-OBn [ No CAS ]

References: [1]Monatshefte fur Chemie,2004,vol. 135,p. 979 - 999.

15
[ 1147-76-8 ]
[ 41036-32-2 ]
[ 736145-05-4 ]

References: [1]Il Farmaco,2004,vol. 59,p. 345 - 352.

16
[ 185990-56-1 ]
[ 41036-32-2 ]
[ 908589-92-4 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2899 - 2911.

17
[ 27460-85-1 ]
[ 41036-32-2 ]
[ 947509-47-9 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 8747 - 8755.

18
[ 41036-32-2 ]
[ 436848-62-3 ]
[ 947189-25-5 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 8747 - 8755.

19
[ 69651-48-5 ]
[ 41036-32-2 ]
[ 947509-48-0 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 8747 - 8755.

20
[ 41036-32-2 ]
(R)-2-[(Diphenyl-phosphinoyl)-phenyl-methyl]-amino}-propionic acid benzyl ester [ No CAS ]

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

21
[ 41036-32-2 ]
[ 92261-95-5 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 5 - 14.

22
[ 41036-32-2 ]
[ 92261-77-3 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 5 - 14.

23
[ 41036-32-2 ]
[ 92261-81-9 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 5 - 14.

24
[ 41036-32-2 ]
[ 374756-15-7 ]

References: [1]Bulletin de la Societe Chimique de France,1969,p. 2743 - 2747.

25
[ 782493-67-8 ]
[ 41036-32-2 ]
C₃₃H₄₂F₃N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; triethylamine; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 20℃; for 168h;	EXAMPLE 76 Step A: D-alanine benzylester p-toluenesulfonic acid salt (22mg, 0. 062MMOL), triethylamine (9. 0muL, 0. 062MMOL), and sodium triacetoxyborohydride (22mg, 0. LOMMOL) were added to a stirring solution of 1-((1R,3S)-3-isopropyl-3-[6-(trifluoromethyl)-2H-1, 3-benzoxazin-3 (4H)- yl] carbonyl} cyclopentyl) piperidin-4-one (19MG, 0.021mmol) in DCM (LOML). The reaction mixture was stirred at rt for 96h, however, the reaction had not gone to completion. Another 39mg (0. 1 LMMOL) OF L- alanine BENZYLESTERP-TOLUENESULFONIC acid salt and 15, UL (0. 1 LMMOL) of triethylamine was added to the reaction mixture. After stirring for an additional 72h at rt, the reaction mixture was diluted with dichloromethane (50ML), washed with sodium bicarbonate solution (1 x 50ML) and brine (1 x 50ML), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by preparatory TLC (silica gel, 0. 25% ammonium hydroxide, 2.25% MeOH, 97.5% DCM) afforded the desired product. ESI-MS calculated for C33H42F3N304 : 601. 70, found 602 (M + H).
	With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20℃; for 168h;	Step A: D-alanine benzylester p-toluenesulfonic acid salt (22 mg, 0.062 mmol), triethylamine (9.0 muL, 0.062 mmol), and sodium triacetoxyborohydride (22 mg, 0.10 mmol) were added to a stirring solution of 1-((1R,3S)-3-isopropyl-3-[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentyl)piperidin-4-one (19 mg, 0.021 mmol) in DCM (10 mL). The reaction mixture was stirred at rt for 96 h, however, the reaction had not gone to completion. Another 39 mg (0.11 mmol) of L-alanine benzylester p-toluenesulfonic acid salt and 15 muL (0.11 mmol) of triethylamine was added to the reaction mixture. After stirring for an additional 72 h at rt, the reaction mixture was diluted with dichloromethane (50 mL), washed with sodium bicarbonate solution (1×50 mL) and brine (1×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by preparatory TLC (silica gel, 0.25% ammonium hydroxide, 2.25% MeOH, 97.5% DCM) afforded the desired product. ESI-MS calculated for C33H42F3N3O4: 601.70. found 602 (M+H).

References: [1]Patent: WO2004/92124,2004,A2 .Location in patent: Page 113.
[2]Patent: US2007/238723,2007,A1 .Location in patent: Page/Page column 61.

26
dibenzylphosphoryl-L-alanyl-L-proline [ No CAS ]
[ 41036-32-2 ]
dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine benzylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In ethyl acetate; N,N-dimethyl-formamide;	Example 14 Dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine L-arginine salt: Dibenzylphosphoryl-L-alanyl-L-proline (1.4 g, 3.2 m mole), HOBt (476 mg, 3.5 m mole) and D-alanine benzylester p-toluene sulfonic acid salt (1.3 g, 3.5 m mole) were dissolved in DMF (5 ml), and WSC (0.64 ml) was added thereto while cooling to -15 C. The reaction was carried out for 3 hours under cooling and then overnight at room temperature. To the reaction solution ethyl acetate (100 ml) was added and the mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order. The mixture was dried with anhydrous sodium sulfate and the thus obtained solution was distilled under reduced pressure to give an oily dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine benzylester material.
	With benzotriazol-1-ol; In ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 14 Dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine L-arginine salt: Dibenzylphosphoryl-L-alanyl-L-proline (1.4 g, 3.2 m mole), HOBt (476 mg, 3.5 m mole) and D-alanine benzylester p-toluene sulfonic acid salt (1.3 g, 3.5 m mole) were dissolved in DMF (5 ml), and WSC (0.64 ml) was added thereto while cooling to -15 C. The reaction was carried out for 3 hours under cooling and then overnight at room temperature. To the reaction solution ethyl acetate (100 ml) was added and the mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order. The mixture was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced, pressure to give oily dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine benzylester.

References: [1]Patent: US4472381,1984,A .
[2]Patent: US4536395,1985,A .

27
[ 926309-49-1 ]
[ 41036-32-2 ]
(R)-2-[(2R,3S,4R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-azido-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylamino}-propionic acid benzyl ester ammonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With dicyclohexyl-carbodiimide; In water; tert-butyl alcohol;	EXAMPLE 6 General Procedure monobasic Salts The appropriate amino acid ester (7 mol equivalent) was added to a solution of the nucleoside 5'-monophosphate species (1 mol equivalent) and DCC (5 mol. equivalent) in tert-BuOH (5 mL) and H2O (2 mL) and the resulting mixture was stirred and heated at reflux for 4 h. The solvent was removed in vacuo to afford the desired salt which was purified as described. ; step 2-azido-cytidine 5'-O-(benzyloxy-D-alaninyl)phosphate The title compound was prepared as described in Example 5 utilizing azido-cytidine monophosphate (100 mg, 0.294 mmol), <strong>[41036-32-2]D-alanine benzyl ester tosylate</strong> salt (14m 368.83 mg, 2.058 mmol), DCC (302.82 mg, 1.47 mmol) in tert-BuOH (5 mL) and H2O. The crude was purified by column chromatography eluting with a gradient starting from iso-PrOH, to iso-PrOH/conc. NH4OH/H2O (90:7:3, 85:10:5 and 80:12:8) to I-68 afford a white solid (7.8 mg, 0.0139 mmol, 7%). 31P NMR (D2O): delta6.52; 1H NMR (D2O): delta7.63 (1H, d, H6-cytidine, J=7.8 Hz), 7.25 (5H, CH-benzyl), 5.91 (1H, d, H1'-cytidine, J=3.0 Hz), 5.86 (1H, d, H5-cytidine, J=7.8 Hz), 5.00 (2H, s, CH2-benzyl), 4.25-4.13 (2H, m, H2'-cytidine, H3'-cytidine), 3.84 (2H, m, CH2 (2H, m, H5'-cytidine), 3.71 (1H, m, CHalpha), 1.37 (3H, d, CH3-lateral chain); MS (ES) m/e: 524.0 (M-, 100%); Accurate mass: C19H23N7O9P required 524.1295 found 524.1295.

References: [1]Patent: US2007/42988,2007,A1 .Location in patent: Page/Page column 19; 43.

28
[ 41036-32-2 ]
[ 770-12-7 ]
phenyl (benzyloxy-D-alaninyl)phosphorochloridate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5520 - 5530.

29
[ 41036-32-2 ]
[ 6622-55-5 ]
[ 1214259-11-6 ]

References: [1]Heterocycles,2010,vol. 81,p. 91 - 115.

30
[ 1708-29-8 ]
[ 41036-32-2 ]
[ 1257236-54-6 ]

Yield	Reaction Conditions	Operation in experiment
78%		Ozone gas was passed into a mixture of 2,5-dihydrofuran (1.994 g, 28.46 mmol), methanol (24 ml_),DCM (100 mL) at -60C,(containing a trace of sudan red), until the red colour disappeared leaving a greyish solution. After removal of excess ozone with nitrogen, sodium cyanotrihydroborate (1.252 g, 19.92 mmol) was added to the solution and the mixture stirred at -500C for 10mins. A solution benzyl (2R)-2-aminopropanoate p-toluenesulfonate salt (5 g, 14.23 mmol) in methanol (10OmL) was added dropwise and the stirring continued at 00C overnight. Acetic acid (0.815 mL, 14.23 mmol) was added and the mixture evaporated. The residue was dissolved in DCM (20OmL) and washed with saturated aqueous NaHCO3 solution. The organic extracts were dried over Na2SO4, filtered and evaporated to an oil. The crude product was purified by flash silica chromatography, elution gradient 15 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford benzyl (2R)-2-morpholin- 4-ylpropanoate (2.75 g, 78 %) as a orange oil; m/z: 250.17 (MH+).

References: [1]Patent: WO2010/136778,2010,A1 .Location in patent: Page/Page column 56.

31
[ 1292320-84-3 ]
[ 41036-32-2 ]
[ 1292320-87-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24h;	III. Dipeptides for absolute configuration determination and alpha/gamma-peptide studies.A number of alpha/gamma-dipeptides were prepared using Fmoc-AMCP and standard coupling reagents. However, all proved recalcitrant to crystallization from a wide range of solvent mixtures via slow evaporation. Boc-AMCP was therefore obtained and dipeptides using either D or L forms of Alanine benzyl ester tosylate were prepared (Scheme 5-3). Scheme 5-3. (a) Coupling of Boc-AMCP to LAla-OBn tosylate; (b) Coupling of Boc-AMCP to DAla-OBn tosylate.BocNH-AMCP-DAla-OBnThe couplings proceeded in moderate yields to provide useful amounts of both dipeptides. The dipeptides were isolated and several crystallization trials were set up using slow evaporation from mixtures of chloroform, ethyl acetate, methanol, heptane, and pentane. A mixture of ethyl acetate and heptane yielded large needles for the Boc-NH-AMCP-DAla-OBn dipeptide. These diffracted into the space group PI and the X-ray crystal structure was solved. The absolute configuration of the AMCP residue was shown to be (R,R) for the ring stereocenters, resulting from the Michael addition using the (S) catalyst. The relative configuration of the stereocenters is trans.

References: [1]Patent: WO2011/47190,2011,A1 .Location in patent: Page/Page column 63-64.
[2]Journal of Organic Chemistry,2013,vol. 78,p. 12351 - 12361.

32
[ 15761-38-3 ]
[ 41036-32-2 ]
N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 6120 - 6123.

33
[ 41036-32-2 ]
L-alanyl-D-alanine benzyl ester hydrochloride [ No CAS ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 6120 - 6123.

34
[ 41036-32-2 ]
C₂₄H₃₆N₄O₇ [ No CAS ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 6120 - 6123.

35
C₂₀H₃₁N₅O₈ [ No CAS ]
[ 41036-32-2 ]
[ 1428244-75-0 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4950 - 4953.

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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H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 41036-32-2

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CAS No.: 41036-32-2

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Product Details of H-D-Ala-OBzl·TosOH

Safety of H-D-Ala-OBzl·TosOH

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

[ 41036-32-2 ] Synthesis Path-Downstream 1~35

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