[ CAS No. 67814-68-0 ] {[proInfo.proName]}

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Quality Control of [ 67814-68-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 67814-68-0 ]

Product Details of [ 67814-68-0 ]

CAS No. :	67814-68-0	MDL No. :	MFCD11113821
Formula :	C₈H₁₄O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	190.19	Pubchem ID :	-
Synonyms :

Safety of [ 67814-68-0 ]

Signal Word:	Class:	N/A
Precautionary Statements:	UN#:	N/A
Hazard Statements:	Packing Group:	N/A

Application In Synthesis of [ 67814-68-0 ]

* 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.

Upstream synthesis route of [ 67814-68-0 ]
Downstream synthetic route of [ 67814-68-0 ]

[ 67814-68-0 ] Synthesis Path-Upstream 1~5

1
[ 67-56-1 ]
[ 67814-68-0 ]
[ 4099-85-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 16 h;	1) Obtaining Methyl 2,3-O-isopropyliden-β-D-ribofuranoside (5) A suspension of D-ribose (4, 10g) in acetone (80 mL) cooled to 0°C was added drop by drop to 2,2-dimethyoxypropane (20 mL) with perchloric acid 70percent (4 mL). It was stirred for two hours at ambient temperature and then methanol (14 mL) was added and the mixture was stirred at ambient temperature for 16 hours. A saturated solution of K₂CO₃ (10 mL) was added and the mixture was partitioned in water (150 mL) and CH₂Cl₂ (70 mL). The aqueous phase was extracted with CH₂Cl₂ (3 x 70 mL). The combined organic phases were dried (Na₂SO₄) and the solvent was evaporated to obtain 13,5 g of compound 5 as a colorless syrup. This same reaction was carried out starting from 20 g of D-ribose, obtaining the desired product with a 100percent yield.

Reference： [1] Patent: EP2241556, 2010, A1, . Location in patent: Page/Page column 8
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053

2
[ 67-56-1 ]
[ 67814-68-0 ]
[ 4099-85-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 4, p. 530 - 537

3
[ 67814-68-0 ]
[ 54622-95-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053

4
[ 67814-68-0 ]
[ 34371-14-7 ]

Reference： [1] Synlett, 2012, # 4, p. 541 - 544

5
[ 67814-68-0 ]
[ 805245-41-4 ]

Reference： [1] Patent: US2005/222185, 2005, A1,

[ 67814-68-0 ] Synthesis Path-Downstream 1~10

1
[ 67814-68-0 ]
[ 360-97-4 ]
[ 85249-90-7 ]
[ 85249-91-8 ]

Reference： [1]Carbohydrate Research,1983,vol. 113,p. 1 - 20

2
(3aR,4R,7R,7aR)-4-(5-Amino-pyrimidin-4-ylamino)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol [ No CAS ]
[ 13754-19-3 ]
[ 67814-68-0 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4964 - 4969

3
[ 67814-68-0 ]
[ 19752-61-5 ]
[ 78119-30-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 723 - 725

4
[ 50-69-1 ]
[ 67-64-1 ]
[ 67814-68-0 ]

Yield	Reaction Conditions	Operation in experiment
92.4%	With sulfuric acid; at 20℃; for 2h;	To a stirred solution of d-ribose (4) (10.0 g, 66.6 mmol) in acetone (100 mL), concd H2SO4 (0.3 mL) was added drop wise at room temperature. And the resulting reaction mixture was stirred at room temperature for 2 h, until TLC showed complete conversion of the starting material. The reaction mixture was neutralized by addition of solid NaHCO3 and filtered to remove inorganic solid. The filtrate was concentrated under reduced pressure to give colorless syrup. The residue was purified by silica gel column chromatography using hexane and ethyl acetate (30%) as the eluent to afford 5 as colorless syrup (11.7 g, 92.4%); Rf 0.4 (50% EtOAc/hexane); -36.7 (c 1.1, acetone); IR (KBr, neat): 869, 1068, 1211, 1376, 1458, 1635, 2940, 2986, 3408; 1H NMR (300 MHz, CDCl3): delta 1.32 (3H, s, CH3), 1.49 (3H, s, CH3), 3.74 (2H, s, CH2OH), 4.41 (1H, s, CHCH2), 4.59 (1H, d, J=6.04 Hz, CH), 4.84 (1H, d, J=5.66 Hz, CH), 5.42 (1H, s, CHOH); 13C NMR (300 MHz, CDCl3): delta 24.5, 26.2, 63.3, 81.5, 86.5, 87.5, 102.5, 112.0; MS (ESI): m/z 213 (M+Na)+; HRMS: calcd for C8H14O5Na: 213.07334. Found 213.07304.
74%	With sulfuric acid; at 20℃; for 2.5h;	(1) The <strong>[50-69-1]D-ribose</strong> (80g, 532.9mmol) was dissolved in acetone 1000ml, added dropwise at room temperature H 2SO 4(2.4 mL) and was stirred stirred at room temperature for 2.5 hours the mixture was neutralized with solid NaHCO 3, Filtered, and concentrated by evaporation under reduced pressure, to give a colorless syrup (. 1A), yield 74%
67.3%	With sulfuric acid; at 20℃;	Step 1. 2,3-O-isopropylidene-D-ribofuranose Into a suspension of <strong>[50-69-1]D-ribose</strong> (50 g, 0.33 mol) in acetone (1500 mL) was added sulfuric acid (1 mL) dropwise. Reaction mixture was stirred overnight at room temperature and then neutralized with sat. aq. NaHCO3. Solution was decanted and concentrated. Oily residue was dissolved in EtOAc (1000 mL) and washed with water (300 mL). Aqueous layer was re-extracted with EtOAc (2*500 mL). Combined extracts were dried over Na2SO4 and concentrated to yield the target compound (42.3 g, 67.3%) as oil which was used as such for the next step.

	With sulfuric acid; at 25℃; for 3h;	A white suspension of (2R,3R,4R)-2,3,4,5-tetrahy- droxypentanal C-1 (150 g, 999 mmol) and conc. H2S04 (9.8 g, 5.33 mE, 99.9 mmol) in acetone (1500 mE) was stirred at room temperature (25 C.) for 3 h. The suspension was almost turned to a clear solution. TEC (petroleum ether/EtOAc=i :1) showed a major spot. 120 g of NaHCO3 was added and stirred for 1 h, then filtered. The filtrate was concentrated to dryness to afford crude C-2 (210 g, >100%) as a colorless oil, which was used in the next step directly without purification.
375 g	With toluene-4-sulfonic acid; at 20 - 25℃;	Into a 5L, 4 necked round-bottomed flask equipped with a mechanical stirrer, a thermometer socket, and a condenser, were charged acetone (3.0 L), <strong>[50-69-1]D-ribose</strong> (300.0 gm, 2.0 mole) and p-toluene sulfonic acid (11.5 gm). The solution was stirred and maintained at 20-25C for 2.5-3.0hrs. After completion of reaction, the reaction mixture was neutralized with aq. base solution and filtered. The filtrate was evaporated to dryness to get 375.0 gm (98.8% by theory) of 2, 3-O-isopropylidene-<strong>[50-69-1]D-ribose</strong> of formula (4a) as light brown colour oily residue. Purity: >95% by GC

Reference： [1]Tetrahedron,2016,vol. 72,p. 7135 - 7142
[2]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 709 - 711
[3]Patent: US2020/93848,2020,A1 .Location in patent: Paragraph 0279-0280; 0283-0284
[4]Tetrahedron,2012,vol. 68,p. 5829 - 5832
[5]Carbohydrate Research,2014,vol. 398,p. 13 - 18
[6]Journal of the American Chemical Society,2020,vol. 142,p. 6409 - 6422
[7]Patent: CN104524593,2017,B .Location in patent: Paragraph 0028-0029
[8]Patent: US2009/48189,2009,A1 .Location in patent: Page/Page column 38
[9]Tetrahedron,1995,vol. 51,p. 6529 - 6540
[10]Organic Letters,2012,vol. 14,p. 2134 - 2137
[11]Patent: US2016/244475,2016,A1 .Location in patent: Paragraph 0237; 0238
[12]Patent: WO2016/189542,2016,A1 .Location in patent: Page/Page column 10; 15; 20

5
[ 67814-68-0 ]
[ 54622-95-6 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4041 - 4053

6
[ 67814-68-0 ]
[ 163226-45-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7742 - 7747

7
[ 67814-68-0 ]
[ 65-86-1 ]
1'-hydroxy-2',3'-O-isopropylidene-5'-O-orotyl-D-ribofuranoside [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 5618 - 5621

8
[ 67814-68-0 ]
[ 65-86-1 ]
1',5'-O-diorotyl-2',3'-O-isopropylidene-D-ribofuranoside [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 5618 - 5621

9
[ 30725-00-9 ]
[ 67814-68-0 ]
[ 70266-87-4 ]

Yield	Reaction Conditions	Operation in experiment
60 % de	With lithium triethylborohydride In tetrahydrofuran; dichloromethane at 0℃; for 0.5h; Overall yield = 90 %; Overall yield = 34 mg;	1.2. Typical procedure for reduction of the sugar lactones to sugar lactols with LTBH General procedure: LTBH (1 M/THF; 0.24 mL, 0.24 mmol) was added to a solution ofthe appropriate sugar lactone (0.2 mmol) in anhydrous CH2Cl2(3 mL) at 0 C. After 30 min, the reaction mixture was quenchedwith MeOH and the volatiles were evaporated. The resulting residuewas dissolved in CH2Cl2 (10 mL) and washed with NaHCO3/H2O. The organic layer was then dried (Mg2SO4), evaporated andthe residue was column chromatographed (7:3 / 1:1, hexane/EtOAc, unless stated otherwise) to afford the corresponding sugarhemiacetals 2, 5, 7, 9, 11, 13, 15, 17, 19, 21, 23, 25 & 27 (see SI Sectionfor synthetic details and spectral characterization for all compounds).Yields and different reaction conditions are described inTable 2.

Reference： [1]Gonzalez, Cesar; Kavoosi, Sam; Sanchez, Andersson; Wnuk, Stanislaw F. [Carbohydrate Research, 2016, vol. 432, p. 17 - 22]

10
[ 67814-68-0 ]
[ 805245-41-4 ]

Reference： [1]Patent: US2005/222185,2005,A1

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[ CAS No. 67814-68-0 ] {[proInfo.proName]}

Quality Control of [ 67814-68-0 ]

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[ 67814-68-0 ] Synthesis Path-Upstream 1~5

[ 67814-68-0 ] Synthesis Path-Downstream 1~10

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