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D-(-)-Tartaric acid diisopropyl ester
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[ CAS No. 62961-64-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 62961-64-2
Chemical Structure| 62961-64-2
Structure of 62961-64-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 62961-64-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 62961-64-2 ]

Product Details of [ 62961-64-2 ]

CAS No. :62961-64-2 MDL No. :MFCD00008876
Formula : C10H18O6 Boiling Point : -
Linear Structure Formula :- InChI Key :XEBCWEDRGPSHQH-YUMQZZPRSA-N
M.W : 234.25 Pubchem ID :112972
Synonyms :

Calculated chemistry of [ 62961-64-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 7
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.08
TPSA : 93.06 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : -0.39
Log Po/w (MLOGP) : -0.09
Log Po/w (SILICOS-IT) : 0.25
Consensus Log Po/w : 0.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.2
Solubility : 14.9 mg/ml ; 0.0637 mol/l
Class : Very soluble
Log S (Ali) : -2.11
Solubility : 1.83 mg/ml ; 0.00781 mol/l
Class : Soluble
Log S (SILICOS-IT) : 0.14
Solubility : 324.0 mg/ml ; 1.38 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.34

Safety of [ 62961-64-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 62961-64-2 ]

* 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 [ 62961-64-2 ]

[ 62961-64-2 ] Synthesis Path-Downstream   1~69

  • 1
  • [ 1069-08-5 ]
  • [ 62961-64-2 ]
  • [ 664302-77-6 ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1967,p. 1907 - 1910
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1967,p. 1990 - 1993
  • 2
  • [ 683-85-2 ]
  • [ 62961-64-2 ]
  • [ 135607-89-5 ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 871 - 876
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 983 - 989
  • 3
  • [ 3402-24-2 ]
  • [ 62961-64-2 ]
  • [ 130332-43-3 ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 871 - 876
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 983 - 989
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1314 - 1315
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1451 - 1452
  • 4
  • [ 62961-64-2 ]
  • [ 127854-45-9 ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
[2]Tetrahedron Letters,1998,vol. 39,p. 2071 - 2074
  • 5
  • [ 62961-64-2 ]
  • [ 72163-81-6 ]
  • [ 135607-90-8 ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1991,vol. 40,p. 871 - 876
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1991,p. 983 - 989
  • 6
  • [ 62961-64-2 ]
  • [ 122038-72-6 ]
  • [ 590-86-3 ]
  • [ 58958-05-7 ]
  • [ 35628-05-8 ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 1502
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 1687 - 1688
  • 7
  • [ 14371-10-9 ]
  • [ 62961-64-2 ]
  • (4S,5S)-2-((E)-Styryl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 1783 - 1784
  • 8
  • [ 62961-64-2 ]
  • [ 18162-48-6 ]
  • [ 147488-97-9 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 9
  • [ 100-39-0 ]
  • [ 62961-64-2 ]
  • [ 171964-40-2 ]
Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 1373 - 1375
[2]Journal of the Chemical Society. Perkin transactions I,1995,p. 2849 - 2854
  • 10
  • [ 97760-26-4 ]
  • [ 62961-64-2 ]
  • C23H28O8S [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 1504 - 1506
  • 11
  • [ 6616-69-9 ]
  • [ 62961-64-2 ]
  • (4'R,5'R,6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-pentylspiro-9H-dibenzo[b,d]pyran-9,2'-[1,3]dioxolane-4',5'-dicarboxylic acid bis-1-methylethyl ester [ No CAS ]
  • (4'R,5'R,6aS,10aS)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-pentylspiro-9H-dibenzo[b,d]pyran-9,2'-[1,3]dioxolane-4',5'-dicarboxylic acid bis-1-methylethyl ester [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7065 - 7068
[2]Journal of Organic Chemistry,1997,vol. 62,p. 7065 - 7068
  • 12
  • [ 62961-64-2 ]
  • (4S,5S)-2-Oxo-2λ4-[1,3,2]dioxathiolane-4,5-dicarboxylic acid diisopropyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 2071 - 2074
  • 13
  • [ 62961-64-2 ]
  • [ 79-04-9 ]
  • [ 226710-55-0 ]
Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 429 - 437
  • 15
  • [ 62961-64-2 ]
  • [ 166329-99-3 ]
  • (4S,5S)-2-dimethylsilyl-4,5-di(isopropylcarbonyl)-1,3,2-dioxaborolane [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11174 - 11175
  • 16
  • [ 62961-64-2 ]
  • [ 2283-11-6 ]
  • [ 664302-77-6 ]
Reference： [1]Heteroatom Chemistry,2003,vol. 14,p. 546 - 550
  • 17
  • [ 590-18-1 ]
  • [ 5419-55-6 ]
  • [ 62961-64-2 ]
  • [ 106357-33-9 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5217 - 5231
[2]Organic Syntheses,2011,vol. 88,p. 181 - 196
  • 18
  • [ 2746-25-0 ]
  • [ 62961-64-2 ]
  • [ 871345-82-3 ]
Reference： [1]Organic Letters,2005,vol. 7,p. 5509 - 5512
  • 19
  • [ 62961-64-2 ]
  • (E)-crotylboronate diethanolamine complex [ No CAS ]
  • [ 99745-86-5 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5217 - 5231
  • 20
  • [ 4406-72-8 ]
  • [ 62961-64-2 ]
  • (+)-diisopropyl tartrate phenylboronic ester [ No CAS ]
Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 784 - 790
[2]Journal of Organometallic Chemistry,2007,vol. 692,p. 784 - 790
  • 21
  • [ 62961-64-2 ]
  • 3-(dimethylphenylsilyl)-5-phenyl-2-((4S,5S)-4,5-diisopropoxycarbonyl-1,3,2-dioxaborolan-2-yl)-1-pentene [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 11174 - 11175
  • 22
  • [ 62961-64-2 ]
  • (4'S,5'S)-25,27-dihydroxy-26,28-(4',5'-di-1-methylethoxycarbonyl-3',6'-dioxa-2',7'-dioxooctylene)-dioxycalix<4>arene [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 429 - 437
  • 23
  • [ 62961-64-2 ]
  • (4'S,5'S)-5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-(4',5'-di-1-methylethoxycarbonyl-3',6'-dioxa-2',7'-dioxooctylene)-dioxycalix<4>arene [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 429 - 437
  • 24
  • [ 62961-64-2 ]
  • (2R,3R)-2-Bromo-3-hydroxy-succinic acid diisopropyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 2071 - 2074
  • 25
  • [ 62961-64-2 ]
  • [ 147489-02-9 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 26
  • [ 62961-64-2 ]
  • [ 147489-00-7 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 27
  • [ 62961-64-2 ]
  • [ 147489-01-8 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 28
  • [ 62961-64-2 ]
  • [ 147488-99-1 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 29
  • [ 62961-64-2 ]
  • [ 147488-98-0 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 364 - 372
  • 30
  • [ 62961-64-2 ]
  • (4S,5S)-2-((1S,2S)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 1783 - 1784
  • 31
  • [ 62961-64-2 ]
  • [ 83541-68-8 ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 32
  • [ 62961-64-2 ]
  • [ 181309-87-5 ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 33
  • [ 62961-64-2 ]
  • (2R,3R)-2-Hydroxy-3-thiocyanato-succinic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 34
  • [ 62961-64-2 ]
  • (2R,3S)-2-Azido-3-hydroxy-succinic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 35
  • [ 62961-64-2 ]
  • (2R,3S)-2-Hydroxy-3-nitrooxy-succinic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 36
  • [ 62961-64-2 ]
  • [ 363139-46-2 ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 37
  • [ 62961-64-2 ]
  • (2R,3S)-2-Benzoyloxy-3-hydroxy-succinic acid diisopropyl ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7538 - 7539
  • 38
  • [ 62961-64-2 ]
  • bis(diisopropyl-D-tartrateglycolato)diboron [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis(dimethylamido)diborane; In toluene; at 100℃; for 1.2h; Diisopropyl D-tartrate (FW: 234. 25 ; 2.34 g, 9.99 mmol) in toluene (20 mL) was heated to 100 C. Tetrakis (dimethylamino) diboron (1.0 g, 5.05 mmol) was added neat within 2 minutes to this solution. After an induction period of about 10 minutes a slow release of ME2NH was observed. The mixture was kept at 100 C for 60 minutes. The solution was cooled to room temperature and analysed by GC and shown to be 78.8% pure. The solvent was removed in vacuo to give a colourless viscous oil of bis (diisopropyl-D-tartrate glycolato) diboron (MF : C2OH32B2012 ; FW: 486.106). This oil slowly crystallised at room temperature or at 0 C. Yield: quantitative; 91.5% pure by GC. mp 85 C. 8 (CDCL3, 200 MHz) 1.26 (d, J=6Hz, 24H); 4.82 (s, 4H); 5.08 (h, J=6Hz; 4H) ppm. 13C 8 (CDCL3, 50 MHz) 21.4 ; 69.9 ; 77.8 ; 168.2 ppm.
Reference： [1]Patent: WO2004/76467,2004,A1 .Location in patent: Page 17
  • 39
  • [ 63511-92-2 ]
  • [ 62961-64-2 ]
  • [ 860314-93-8 ]
YieldReaction ConditionsOperation in experiment
55% With pyridinium p-toluenesulfonate; In ethanol; benzene; at 95℃; for 7h; Step B. diisopropyl (4S,5S)-2-[(1E)-prop-1-enyl]-1,3-dioxolane-4,5-dicarboxylate A solution of (2E)-1,1-diethoxybut-2-ene (32.20 g, 223.27 mmol), (-)-diisopropyl D-tartrate (64.64 mL, 245.60 mmol) and pyridinium tosylate (2.24 g, 8.93 mmol) in 100 mL benzene was heated to 95 C. to distill off the solvent and EtOH produced. After 7 h at 95 C., the reaction was cooled to rt and concentrated in vacuo. Purification by normal phase chromatography (10->30% EtOAc/hexanes) yielded 35.37 g (55%) of diisopropyl (4S,5S)-2-[(1E)-prop-1-enyl]-1,3-dioxolane-4,5-dicarboxylate as an orange oil. 1H NMR (CDCl3, 400 MHz) 6.03 (m, 1H); 5.86 (m, 2H); 5.12 (m, 2H); 4.71 (d, J=3.84 Hz, 1H); 4.63 (d, J=3.84 Hz, 1H); 1.78 (m, 3H); 1.30 (d, J=6.23 Hz, 12H); LC/MS [M+H]+=287.
55% With pyridinium p-toluenesulfonate; In benzene; at 95℃; for 7h; Step B. diisopropyl (4S,5S)-2-[(lE)-prop-l-enyl]-1,3-dioxolane-4,5-dicarboxylate; A solution of (2E)-1,1-diethoxybut-2-ene (32.20 g, 223.27 mmol), (-) -diisopropyl D-tartrate (64.64 mL, 245.60 mmol) and pyridinium tosylate (2.24 g, 8.93 mmol) in 100 mL benzene was heated to 95 C to distill off the solvent and EtOH produced. After 7 h at 95 C, the reaction was cooled to rt and concentrated in vacuo. Purification by normal phase chromatography (10->30% EtOAc/hexanes) yielded 35.37 g (55%) of diisopropyl (4S,5S)-2-[(lE)-prop-l-enyl]-1,3-dioxolane-4,5-dicaxboxylate as an orange oil. 1H NMR (CDC13, 400 MHz) 6.03 (m, 1H); 5.86 (m, 2H) ; 5.12 (m, 2H) ; 4.71 (d, J = 3.84 Hz, 1H); 4.63 (d, J = 3.84 Hz, 1H) ; 1.78 (m, 3H) ; 1.30 (d, J = 6.23 Hz, 12H) ; LC/MS [M+H] + = 287
Reference： [1]Patent: US2007/142634,2007,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2005/103043,2005,A1 .Location in patent: Page/Page column 60
  • 40
  • [ 150-46-9 ]
  • [ 60656-87-3 ]
  • [ 62961-64-2 ]
  • [ 1730-25-2 ]
  • [ 161857-05-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydroxide; magnesium sulfate; In diethyl ether; water; toluene; EXAMPLE 208 (R)-1-Phenoxy-5-hexen-2-ol Under anhydrous conditions at -78 C., 475 ml of 1M solution of allylmagnesium bromide in diethyl ether and 60 ml of triethyl borate in 400 ml of diethyl ether are added simultaneously, but separately, to 400 ml of diethyl ether. The reaction is stirred at -78 C. for 3 hours, warmed to 0 C., 450 ml of 2N hydrochloric acid is added carefully and stirred at room temperature for 2 hours. The layers are separated and the organic layer is dried over magnesium sulfate. The diethyl ether layer is filtered and concentrated N vacuo to 100 ml. The residue is dissolved in 400 ml of diethyl ether and treated with 77.8 g of (-)-diisopropyl D-tartrate. The reaction is stirred overnight at room temperature under argon. Ten grams of magnesium sulfate is added and the mixture stirred for 20 minutes, filtered and concentrated in vacuo. The residue is purified by Kugelrohr distillation (at 0.15mm Hg, bp 100-130 C.) to give 72.30 g of the desired borate ester. Under anhydrous conditions (argon) at -78 C., 20.24 g of (phenylmethoxy)acetaldehyde in 17.35 ml of toluene is added to a mixture of 72.3 g of borate ester in 1000 ml of toluene and 54.22 g of 4A molecular sieves. The mixture is stirred at -78 C. for 16 hours. The reaction is filtered, the sieves washed with toluene and the filtrate is poured into 800 ml of water. The layers are separated, the organic layer dried and concentrated in vacuo. The residue is redissolved in 725 ml of diethyl ether and treated with 1M potassium hydroxide for 24 hours at room temperature. The layers are separated, the organic layer is washed with saturated sodium bicarbonate, dried and concentrated in vacuo. The residue is purified by Kugelrohr distillation (1-2mm Hg, bp 100-110 C.) to give 10.44 g of the desired product. Calcd. C12 H16 O2: C: 74.69; H: 8.39 Found: C: 74.69; H: 8.42
Reference： [1]Patent: US5602118,1997,A
  • 41
  • [ 922-65-6 ]
  • [ 62961-64-2 ]
  • (2R,3S)-3-benzyloxy-1,2-epoxy-4-pentene [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1 (3R,4S)3-Benzyloxy-4,5-epoxy-1-pentene (4) STR9 Prepared from 3-hydroxy 1,4-pentadiene by a modified procedure of R. E. Babine, Tetrahedron Letters, 1987, 27, 5791, using diisopropyl-D-tartrate instead of the L form. Analysis showed: Optical Rotation: [alpha]D25 =-25.3 CH2 Cl2, C=1.03: IR (CHCl3) lambdamax 1075 cm-1; 13C NMR (CDCl3, 75.5 MHZ) delta138.0, 134.4, 128.3, 127.58, 27.53, 119.4, 79.2, 70.5, 53.1, 44.7.
Reference： [1]Patent: US5087703,1992,A
  • 42
  • [ 62961-64-2 ]
  • [ 762-72-1 ]
  • [ 955371-49-0 ]
Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6699 - 6702
  • 43
  • [ 62961-64-2 ]
  • [ 122038-72-6 ]
  • (2S,3S)-diisopropyltartrate of isoprenylboric acid [ No CAS ]
Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 1502
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 1687 - 1688
  • 44
  • [ 5419-55-6 ]
  • [ 624-64-6 ]
  • [ 865-47-4 ]
  • [ 62961-64-2 ]
  • [ 99745-86-5 ]
Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6339 - 6348
  • 45
  • (E)-crotylboronate diethanolamine complex [ No CAS ]
  • [ 62961-64-2 ]
  • [ 99745-86-5 ]
Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 6339 - 6348
  • 46
  • [ 546-68-9 ]
  • [ 75-91-2 ]
  • [ 150199-03-4 ]
  • [ 62961-64-2 ]
  • [ 126639-95-0 ]
  • CH3(CH2)4CH(OH)C2H2OSn(CH2CH2CH2CH3)3 [ No CAS ]
Reference： [1]Chemistry Letters,1987,p. 1523 - 1526
  • 47
  • [ 688-61-9 ]
  • [ 62961-64-2 ]
  • (+)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic acid bis(1'-methylethyl) ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 8186 - 8190
  • 48
  • [ 546-68-9 ]
  • [ 62961-64-2 ]
  • (+)-Cinchonine [ No CAS ]
  • Ti2(S,S-diisopropyltartrate)2[(+)-Ocin](O(i)Pr)3 [ No CAS ]
Reference： [1]Canadian Journal of Chemistry,1995,vol. 73,p. 401 - 413
  • 49
  • [ 611228-17-2 ]
  • [ 83816-41-5 ]
  • [ 62961-64-2 ]
  • [ 866452-96-2 ]
YieldReaction ConditionsOperation in experiment
80% To a solution of the allenyl boronic acid (518 mg, 6.18 mmol) in toluene (20 ml) were added molecular sieves (3.0 g) and diisopropyl-D-tartrate (2.6 ml, 12.36 mmol) and the resulting solution was allowed to stand at room temperature for 24 h with gentle stirring from time to time. The obtained solution of chiral allenyl boronic ester was then canulated to a new flask and cooled at -78 C. At this point a solution of the aldehyde from Example 15 (665 mg, 1.9 mmol) in toluene (10 ml) was added through a double tipped needle and the reaction mixture was stirred at -78 C. for 12 h and then warmed up slowly at room temperature overnight. The resulting solution was then quenched with a diluted solution of HCl, extracted with ether and it was then washed with brine, dried and concentrated. Flash column chromatography (silica gel, 5% ethyl acetate/hexanes) afforded the pure product as a colorless liquid (592 mg, 1.52 mmol, 80% yield). To a solution of the obtained alcohol product (592 mg, 1.52 mmol) in CH2Cl2 (10 ml) were added dropwise at 0 C. 2,6-lutidine (0.40 ml, 3.34 mmol) and tert-butyldimethylsilyloxy triflate (0.41 ml, 2.28 mmol). The reaction mixture was warmed up to room temperature and stirred for 4 hours. The resulting solution was then poured into a solution of saturated NH4Cl and extracted with diethyl ether. The combined extracts were dried and concentrated. Flash column chromatography (silica gel, 2% ethyl acetate/hexanes) afforded the pure product (4.4) as a colorless liquid in 95% yield. 1H NMR (250 MHz, CDCl3): delta6.52 (dd, J=15.5 Hz and 10.9 Hz, 1H), 6.26 (dd, J=15.2 and 11.0 Hz, 1H), 5.85 (dd, J=15.5 Hz and 5.3 Hz, 1H), 5.10 (d, J=16.2 Hz, 1H), 4.51 (t, J=5.6 Hz, 1H), 4.31 (q, J=5.9 Hz, 1H), 3.54 (s, 3H), 2.45 (m, 4H), 1.95 (t, J=1.4 Hz, 1H), 1.82 (m, 4H), 0.97 (s, 18H), 0.18 (s, 3H), 0.12 (s, 3H), 0.07 (s, 3H), 0.05 (s, 3H). 13C NMR (62 MHz, CDCl3): delta173.891, 140.738, 137.433, 129.200, 111.125, 93.363, 83.432, 80.947, 71.306, 70.197, 63.012, 51.452, 37.889, 33.516, 28.296, 25.792, 20.566, 18.075, -4.419, -4.578, -4.861, -5.014.
Reference： [1]Patent: US2003/236423,2003,A1 .Location in patent: Page 8; 18-19
  • 50
  • [ 62961-64-2 ]
  • [ 924-53-8 ]
Reference： [1]Organic Letters,2008,vol. 10,p. 3165 - 3167
  • 51
  • [ 627-20-3 ]
  • [ 62961-64-2 ]
  • C15H25BO6 [ No CAS ]
Reference： [1]Organic Letters,2008,vol. 10,p. 2139 - 2142
  • 52
  • [ 83816-41-5 ]
  • [ 62961-64-2 ]
  • [ 92358-44-6 ]
Reference： [1]Organic Letters,2010,vol. 12,p. 988 - 991
  • 53
  • [ 504-61-0 ]
  • [ 62961-64-2 ]
  • [ 98-59-9 ]
  • [ 107033-47-6 ]
Reference： [1]Chemical Communications,2010,vol. 46,p. 3953 - 3954
  • 54
  • [ 62961-64-2 ]
  • [ 136880-74-5 ]
  • [ 99745-86-5 ]
Reference： [1]Tetrahedron,2010,vol. 66,p. 6462 - 6467
  • 55
  • [ 12636-72-5 ]
  • [ 62961-64-2 ]
  • Zr2O2(C5H5)4(C2H2O(CO2CH(CH3)2)2)2 [ No CAS ]
Reference： [1]Angewandte Chemie,1991,vol. 103,p. 1371 - 1373
  • 56
  • [ 24396-24-5 ]
  • [ 62961-64-2 ]
  • [ 1351353-26-8 ]
Reference： [1]Molecules,2011,vol. 16,p. 6806 - 6815
  • 57
  • [ 62961-64-2 ]
  • [ 38982-41-1 ]
  • [ 1411940-86-7 ]
YieldReaction ConditionsOperation in experiment
39% pyridinium p-toluenesulfonate; In benzene; at 90℃; for 15h; To a solution of (E)-4,4-diethoxybut-2-enyl acetate 4 (75 g, 0.37 mol) and diisopropyl(-)-(S,S)-tartrate (86.8g, 0.3 mol) in 800 ml benzene, added PPTS (4.66 g, 0.0185 mol), the mixture was heated to 9 C to distill off the ethanol for 15 hours . The mixture was cooled to r.t. and concentrated in vacuum. Purified with distillation to give Compound 5 (50.0 g, 39%) as a colorless oil. 1 H NMR: (CDCI3, 400 MHz) delta:6.04- 6.01 (m, 1 H), 5.81 -5.80 (m , 1 H), 5.57(d, J = 8Hz , 1 H), 5.07-5.01 (m, 2H), 4.65(d, J = 4 Hz, 1 H), 4.57 (d, J = 4 Hz, 1 H), 4.54-4.53 (m, 2H), 1.99(s, 3H), 1.23-1 .19(m, 12H).
Reference： [1]Patent: WO2012/154204,2012,A1 .Location in patent: Page/Page column 46; 47
  • 58
  • [ 5419-55-6 ]
  • [ 624-64-6 ]
  • [ 62961-64-2 ]
  • [ 99745-86-5 ]
Reference： [1]Organic Syntheses,2011,vol. 88,p. 181 - 196
  • 59
  • [ 62961-64-2 ]
  • [ 77-76-9 ]
  • [ 81327-47-1 ]
Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3860 - 3863
  • 60
  • [ 104-54-1 ]
  • [ 62961-64-2 ]
  • [ 104196-23-8 ]
Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 4274 - 4278
    Angew. Chem.,2015,vol. 127,p. 4348 - 4352,5
  • 61
  • [ 62961-64-2 ]
  • [ 77-76-9 ]
  • bis(1-methylethyl) (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate [ No CAS ]
Reference： [1]Helvetica Chimica Acta,2015,vol. 98,p. 509 - 514
  • 62
  • [ 62961-64-2 ]
  • isopropyl (2S,3R)-3,4-dihydroxy-2-((triisopropylsilyl)oxy)butanoate [ No CAS ]
Reference： [1]Patent: WO2016/201225,2016,A1
  • 63
  • [ 62961-64-2 ]
  • isopropyl (S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-((triisopropylsilyl)oxy)acetate [ No CAS ]
Reference： [1]Patent: WO2016/201225,2016,A1
  • 64
  • [ 62961-64-2 ]
  • isopropyl (S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate [ No CAS ]
Reference： [1]Patent: WO2016/201225,2016,A1
  • 65
  • [ 62961-64-2 ]
  • isopropyl (S)-2-((2’,5’-difluoro-3-nitro-[1,1‘-biphenyl]-4-yl)oxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate [ No CAS ]
Reference： [1]Patent: WO2016/201225,2016,A1
  • 66
  • [ 80522-42-5 ]
  • [ 62961-64-2 ]
  • diisopropyl (2S,3S)-2-hydroxy-3-((triisopropylsilyl)oxy)succinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 2,6-dimethylpyridine; In dichloromethane; at 20℃; 2,6-Dimethylpyridine (11 g, 102.66 mmol) was added dropwise to a stirred solution of diisopropyl (2S,3S)-2,3-dihydroxysuccinate (20 g, 85.38 mmol) and triisopropylsilyl trifluoromethanesulfonate (31 g, 102 mmol) in dichloromethane (400 mL). The mixture was stirred overnight at room temperature. Then, the mixture was washed with saturated ammonium chloride, dried (Na2SO4), and concentrated. The resulting residue was purified via MPLC cluting with 10% ethyl acetate in petroleum ether to afford diisopropyl (2S,3S)-2- hydroxy-3-((triisopropylsilyl)oxy)succinate (20 g, 55%) as a colorless oil.
Reference： [1]Patent: WO2016/201225,2016,A1 .Location in patent: Paragraph 0003777
  • 67
  • [ 62961-64-2 ]
  • diisopropyl diazenedicarboxylate [ No CAS ]
Reference： [1]Catalysis science and technology,2017,vol. 7,p. 5644 - 5649
  • 68
  • [ 62961-64-2 ]
  • [ 75-03-6 ]
  • diisopropyl (O,O'-diethyl)-L-tartrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% 4.10 g of 60 wt% NaH (Mw = 24.0, 0.10 mol) were added to 150 mL of dry N, N'-dimethylformamide,Cool to 0 C.At this temperature, 11.8 g (Mw = 234.5, 0.05 mol)L - (+) - diisopropyl tartrate) in dry N, N'-dimethylformamide,After the addition was completed, the mixture was stirred for 1 hour at below 5 C.While maintaining this temperature, a solution of 23.4 g of ethyl iodide (Mw = 156, 0.150 mol) in dry N, N'-dimethylformamide was added,Dropping is completed,0 C for half an hour,Heated to 20 C to continue the reaction for 2 hours,Heated to 60 C for 4 hours,End the reaction.Add 100mL water,Ether three times.Liquid separation.Organic combination,Dried over anhydrous magnesium sulfate,filter,Spin the filtrate,Vacuum distillation,The fractions were collected to give the product 10.8g,Yield 74%.
Reference： [1]Patent: CN104610062,2017,B .Location in patent: Paragraph 0073; 0074; 0075
  • 69
  • [ 62961-64-2 ]
  • [ 860314-94-9 ]
Reference： [1]Patent: WO2005/103043,2005,A1
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