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Cas Database

2406-22-6

2406-22-6

Identification

  • Product Name:1,2-Propanediol, 2-phenyl-, (2S)-

  • CAS Number: 2406-22-6

  • EINECS:

  • Molecular Weight:152.193

  • Molecular Formula: C9H12O2

  • HS Code:2906299090

  • Mol File:2406-22-6.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 105 Articles be found

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

Sánchez-Chávez, Anahí C.,Elena Vargas-Díaz, Ma.,Ontiveros-Rodríguez, Julio C.,Pérez-Estrada, Salvador,Flores-Bernal, Gustavo G.,Mendoza-Espinosa, Daniel,álvarez-Hernández, Alejandro,Delgado, Francisco,Tamariz, Joaquín,Gerardo Zepeda-Vallejo

, p. 4437 - 4441 (2018)

The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

The Bovine Serum Albumin-2-Phenylpropane-1,2-diolatodioxo-osmium(VI) Complex as an Enantioselective Catalyst for cis-Hydroxylation of Alkenes

Kokubo, Toshio,Sugimoto, Toyonari,Uchida, Toshio,Tanimoto, Shigeo,Okano, Masaya

, p. 769 - 770 (1983)

The 1:1 complex between an osmate ester and bovine serum albumin was found to be effective as an enantioselective catalyst in the cis-hydroxylation of alkenes, affording diols in up to 68percent e.e. and turnover of the catalyst with tert-butyl hydroperoxide.

Chiral-auxiliary-controlled diastereoselectivity in the epoxidation of enecarbamates with DMD and mCPBA

Adam, Waldemar,Bosio, Sara G.,Wolff, Barbara T.

, p. 819 - 822 (2003)

(Matrix presented) Chiral oxazolidinone-substituted enecarbamates 1 are epoxidized in a diastereoselectivity up to 93:7 for both DMD and mCPBA. The diastereofacial differentiation depends on the steric interaction between the R1 substituent on the oxazolidinone ring and the incoming electrophile. The stereochemical course of epoxidation was assessed by chemical correlation with the known optically active diols.

New 2-acyl-1,3-dioxane derivatives from (1R)-(-)-myrtenal: stereochemical effect on their relative ability as chiral auxiliaries

Becerra-Martinez, Elvia,Velazquez-Ponce, Pedro,Sanchez-Aguilar, Miguel A.,Rodriguez-Hosteguin, Alfredo,Joseph-Nathan, Pedro,Tamariz, Joaquin,Zepeda, L. Gerardo

, p. 2727 - 2737 (2007)

Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (1R)-(-)-myrtenal 2, were treated with (RO)2CHCOR3 (R3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, ≥88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions.

An improved version of the Sharpless asymmetric dihydroxylation

Mehltretter,Dobler,Sundermeier,Beller

, p. 8083 - 8087 (2000)

The osmium catalyzed asymmetric dihydroxylation of olefins (Sharpless AD) was studied under controlled pH conditions. It was found that providing a constant pH value of 12.0 leads to improved reaction rates for internal olefins. Hydrolysis aids such as methanesulfonamide can be omitted. For terminal olefins, working at a constant pH of 10.0 at room temperature leads to higher enantioselectivities compared to AD reactions without pH control. (C) 2000 Elsevier Science Ltd.

Catalytic asymmetric dihydroxylation of α-methylstyrene by air

Krief, Alain,Colaux-Castillo, Catherine

, p. 4189 - 4192 (1999)

Dioxygen is able, under visible irradiation, to promote the high yielding and highly asymmetric dihydroxylation of α-methylstyrene in the presence of catalytic amounts of Os(VI), phthalazine dihydroquinidine chiral ligand [(DHQD)2PHAL].

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Torabi Kohlbouni, Saeedeh,Sarkar, Aritra,Zhang, Jun,Li, Xiaoyong,Borhan, Babak

supporting information, p. 817 - 823 (2020/03/26)

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions

Blumberg, Shawn,Martin, Stephen F.

, p. 7 - 14 (2020/10/08)

K3Fe(CN)6 and NaIO4 serve as catalytic co-oxidants for osmium-catalyzed dihydroxylations that are performed under near-neutral conditions with K2S2O8 as the stoichiometric oxidant and Na2HPO4 as the base. By using either quinuclidine or hydroquinidine 1,4-phthalazinediyl ether [(DHQD)2Phal], good yields of racemic or enantioenriched diols are obtained. This simple, biphasic procedure offers advantages over other neutral dihydroxylation protocols that use N-methylmorpholine oxide as the stoichiometric oxidant, by suppressing the secondary catalytic cycle that leads to reduced enantioselectivities. The utility of the procedure, which is nicely suited for base-labile starting materials or products, is demonstrated by performing the dihydroxylation in the presence of an aliphatic aldehyde moiety.

Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration

Bochat, Andrew J.,Shoba, Veronika M.,Takacs, James M.

, p. 9434 - 9438 (2019/06/27)

Regiocontrol in the rhodium-catalyzed boration of vinyl arenes is typically dominated by the presence of the conjugated aryl substituent. However, small differences in TADDOL-derived chiral monophosphite ligands can override this effect and direct rhodium-catalyzed hydroboration of β-aryl and β-heteroaryl methylidenes by pinacolborane to selectively produce either chiral primary or tertiary borated products. The regiodivergent behavior is coupled with enantiodivergent addition of the borane. The nature of the TADDOL backbone substituents and that of the phosphite moiety function synergistically to direct the sense and extent of regioselectivity and enantioinduction. Twenty substrates are shown to undergo each reaction mode with regioselectivity values reaching greater than 20:1 and enantiomer ratios reaching up to 98:2. A variety of subsequent transformations illustrate the potential utility of each product.

Syn-dihydroxylation of alkenes using a sterically demanding cyclic diacyl peroxide

Pilevar, Afsaneh,Hosseini, Abolfazl,Becker, Jonathan,Schreiner, Peter R.

, p. 12377 - 12386 (2019/10/11)

The syn-dihydroxylation of alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent P4 also shows an improved selectivity for dihydroxylation of alkenes bearing β-hydrogens as compared to other CAPs, where both diol and allyl alcohol products compete with each other. Furthermore, the use of enantiopure P4 (labeled P4′) demonstrates the potential of P4′ for a metal-free asymmetric syn-dihydroxylation of alkenes.

Process route upstream and downstream products

Process route

3-hydroxy-2-phenylpropene
6006-81-1

3-hydroxy-2-phenylpropene

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
isopropenylbenzene; With C9H10O4; In chloroform; water; at 40 ℃; for 24h; Sealed tube;
With water; sodium hydroxide; In 1,4-dioxane; at 100 ℃; for 48h; Sealed tube;
64%
16%
Conditions
Conditions Yield
With K2; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 25 ℃; for 1.6h; pH=10.0;
95%
With potassium osmate(VI) dihydrate; potassium carbonate; 3-[(3-cholamidopropyl)dimethylammonio]propanesulfonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; at 20 ℃; for 48h; optical yield given as %ee;
95%
With AD-Mix-β; water; In tert-butyl alcohol; at 0 ℃; for 10h;
93%
With osmium(VIII) oxide; (DHQD)2PHAL; dihydrogen peroxide; In tert-butyl alcohol; at 0 ℃;
88%
With methanesulfonamide; AD-mix β; water; In ethanol; at 4 ℃; for 24h;
82%
With potassium osmate(VI); disodium hydrogenphosphate; dipotassium peroxodisulfate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; Reagent/catalyst; enantioselective reaction;
72%
isopropenylbenzene; With 2,2'-bis(1,3,2-benzodioxaborole); (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)rhodium (I); (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline; In tetrahydrofuran; at 20 ℃; for 12h;
With dihydrogen peroxide; Product distribution / selectivity;
67%
With AD-mix-β; In water; tert-butyl alcohol; at 0 ℃; for 18h;
With potassium osmate(VI); Benzyl phenyl selenoxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 3h; Mechanism; assymetric dihydroxylation in various reaction conditions;
With potassium osmate(VI); Benzyl phenyl selenoxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 3h; Yield given;
With potassium osmate(VI) dihydrate; streptavidin S112M mutant; potassium carbonate; potassium hexacyanoferrate(III); In water; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;
(R)-1-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(4-methoxyphenyl)methoxy)-2-phenylpropan-2-ol
1632157-22-2

(R)-1-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(4-methoxyphenyl)methoxy)-2-phenylpropan-2-ol

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 - 20 ℃; for 5h;
67%
(R)-2-hydroxy-2-phenylpropanaldehyde
4361-50-6,69489-14-1,71350-62-4

(R)-2-hydroxy-2-phenylpropanaldehyde

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; at 23 ℃; for 1.5h;
66%
With sodium tetrahydroborate; In ethanol; at 0 ℃;
With sodium tetrahydroborate; In ethanol; for 1h; Yield given; Ambient temperature;
With sodium tetrahydroborate; In ethanol; at 0 ℃; Yield given;
With sodium tetrahydroborate; In water; tert-butyl alcohol; at 0 ℃; for 2h; Inert atmosphere;
11 mg
Conditions
Conditions Yield
With phosphoric acid; In water; toluene;
94.5%
(2S)-2-phenylpropane-1,2-diol
2406-22-6

(2S)-2-phenylpropane-1,2-diol

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; DHQD-PHAL-OPEG-OMe; In water; tert-butyl alcohol; at 0 ℃; for 24h; Title compound not separated from byproducts;
89%
With P. oryzae (IFO 31177); at 24 ℃; Product distribution; various phenylpropenes, stereoselectivity;
With PHTHALAZINE; osmium(VIII) oxide; dihydrogen peroxide; dihydroquinidine; Product distribution; other reagent;
With osmium(VIII) oxide; 2,5-diphenyl-4,6-diquinine-pyrimidine-ethylene glycol dimethacrylate -polymer; at 20 ℃; for 20h; Product distribution;
With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL; water; potassium carbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With osmium(VIII) oxide; (DHQ)2-DP-PHAL; Title compound not separated from byproducts;
With osmium(VIII) oxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 3h; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); water; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With osmium(VIII) oxide; sodium hydrogensulfite; bispiperazine (2d); In toluene; at -78 ℃; Yield given. Yields of byproduct given;
With osmium(VIII) oxide; 2,3-diphenyl-5,8-bis-(9-O-dihydroquinidine)pyrazino<2,3-d>pyridazine; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 30h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; further cond.: electrolytic method;
With osmium(VIII) oxide; (S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine; In tetrahydrofuran; at -78 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With MeO-PEG-modified DHQD; potassium carbonate; potassium hexacyanoferrate(III); for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With AD-mix-α; In water; tert-butyl alcohol; at 0 ℃; for 6h; Title compound not separated from byproducts;
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 28h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With phosphate buffer; oxygen; K2; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tert-butyl alcohol; at 50 ℃; under 750.06 Torr; pH=10.4; Title compound not separated from byproducts;
With air; hydroquinone 1,4-phthalazinediyl diether; K2; In water; tert-butyl alcohol; at 50 ℃; for 24h; under 15001.2 Torr; pH=10.4;
With potassium dioxotetrahydroxoosmate(VI); Benzyl phenyl selenoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium carbonate; In tert-butyl alcohol; at 20 ℃; Further Variations:; Reagents; Time; Product distribution;
With (DHQD)2PHAL; K2; oxygen; In water; tert-butyl alcohol; at 50 ℃; for 24h; under 750.06 Torr; pH=10.4; Title compound not separated from byproducts;
With potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); osmium(VIII) oxide; PEM-MC OsO4; In acetone; at 30 ℃; for 5h; Title compound not separated from byproducts;
With osmium(VIII) oxide; tetraethylammonium acetate; dihydrogen peroxide; quinidine based chiral catalyst; In water; tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
With Resin-OsO4; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; for 24h; Further Variations:; Reagents; 6; Product distribution;
With osmium(VIII) oxide; (QN)2PHAL; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; Title compound not separated from byproducts;
With 4-methyl-morpholine; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; dihydrogen peroxide; LDH-OsW; In tert-butyl alcohol; at 20 ℃; for 2h; Further Variations:; Reagents; Catalysts; Product distribution;
With sodium hypochlorite; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; K2; In water; tert-butyl alcohol; at 0 ℃; for 1h; pH=12.7; Further Variations:; Solvents; Reagents; Temperatures; Product distribution;
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); block copolymer-supported bis-cinchona alkaloid ligand; In water; toluene; tert-butyl alcohol; at 0 ℃; for 24h; Title compound not separated from byproducts;
With sodium chlorite; potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; sodium hydroxide; potassium chloride; In water; tert-butyl alcohol; at 0 - 1 ℃; for 1h; pH=11.8; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium carbonate; In water; tert-butyl alcohol; at 20 ℃; for 24h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; NAP-Mg-OsO4; In water; tert-butyl alcohol; at 20 ℃; for 15h; Title compound not separated from byproducts;
With K2OsO2(OH)2; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; [C4mim]NTf2; at 20 ℃; for 24h; Further Variations:; Reagents; Product distribution;
isopropenylbenzene; With Triton X-114; potassium carbonate; potassium hexacyanoferrate(III); divinylbenzene)polystyrene resin-microencapsulated Os; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; at 30 ℃; for 24h;
With sulfuric acid; In water; at 30 ℃; for 0.166667h; Title compound not separated from byproducts;
With osmium(VIII) oxide; chiral polysiloxane-bound ligand; 4-methylmorpholine N-oxide; In acetone; at 0 - 4 ℃; for 2h; Further Variations:; Reagents; reaction time; Product distribution;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
With (DHQ)2-PHAL-S-(CH2)6OH on magnetic mesocellular -porous SiO2; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; In water; tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
isopropenylbenzene; With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); hydroquinidein 1,4-phthalazinediyl diether; In water; tert-butyl alcohol; at 20 ℃;
With ethyl vinyl ether; In water; tert-butyl alcohol; at 20 ℃; for 1h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4; In water; tert-butyl alcohol; at 20 ℃; for 12h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; polyaniline-supported Os; In water; acetone; acetonitrile; at 20 ℃; for 12h; Title compound not separated from byproducts;
With osmium(VIII) oxide; (DNQD)2PHAL; tetraethylammonium acetate; methyltrioxorhenium(VII); In tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts.;
With 4-methyl-morpholine; tetraethylammonium acetate; titanium silicate; silica gel*cinchona alkaloid*K2OsO4*2H2O; In water; tert-butyl alcohol; at 20 ℃; for 13h; Title compound not separated from byproducts.;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; Triton X-114; potassium hexacyanoferrate(III); OsO4 poly[(PhO-EtO-Me-styrene)-co-styrene] microcapsules; In water; at 30 ℃; for 24h; Title compound not separated from byproducts.;
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; chiral triazine catalyst; In water; tert-butyl alcohol; at 0 ℃; for 14h; Title compound not separated from byproducts.;
With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; In water; toluene; tert-butyl alcohol; at 25 ℃; for 21h; Title compound not separated from byproducts.;
With carbon dioxide; dihydrogen peroxide; osmium(VIII) oxide; In water; acetone; at 25 ℃; under 760.051 Torr; Title compound not separated from byproducts.;
With potassium osmate(VI) dihydrate; dodecyltrimethylammonium bromide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; at 20 ℃; for 48h; optical yield given as %ee;
With N,N'-ethane-1,2-diyl-N,N'-[3,5-bis[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy]benzyloxy]-N,N,N',N'-tetramethylammonium dibromide; C120H134N2O28(2+)*O4Os(2-); water; 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; In acetonitrile; at 20 ℃; for 0.5h; enantioselective reaction; Inert atmosphere;
With potassium osmate(VI) dihydrate; streptavidin L124K mutant; potassium carbonate; potassium hexacyanoferrate(III); In water; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;
With seleno-L-cystine; water; dihydrogen peroxide; at 20 ℃; for 240h; Overall yield = 68 %; stereoselective reaction;
20 % ee
isopropenylbenzene; With (+)-[Rh((S,S)-Phebox-i-Pr)OAc2(H2O)]; bis(pinacol)diborane; sodium t-butanolate; In tetrahydrofuran; at 60 ℃; for 1h; Inert atmosphere;
In tetrahydrofuran; water; at 20 ℃; for 1h; enantioselective reaction; Inert atmosphere;
76 % ee
With alpha-D-glucopyranose; Escherichia coli (SST1); In Hexadecane; at 30 ℃; for 8h; pH=8; Overall yield = 24 %Chromat.; enantioselective reaction; Green chemistry; Enzymatic reaction;
46 % ee
With D-glucose; In aq. phosphate buffer; Hexadecane; at 30 ℃; for 8h; pH=8; Overall yield = 24 %Chromat.; Microbiological reaction;
46.8 % ee
(2S)-2-phenylpropane-1,2-diol
2406-22-6

(2S)-2-phenylpropane-1,2-diol

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; DHQD-PHAL-OPEG-OMe; In water; tert-butyl alcohol; at 0 ℃; for 24h; Title compound not separated from byproducts;
89%
With P. oryzae (IFO 31177); at 24 ℃; Product distribution; various phenylpropenes, stereoselectivity;
With PHTHALAZINE; osmium(VIII) oxide; dihydrogen peroxide; dihydroquinidine; Product distribution; other reagent;
With osmium(VIII) oxide; 2,5-diphenyl-4,6-diquinine-pyrimidine-ethylene glycol dimethacrylate -polymer; at 20 ℃; for 20h; Product distribution;
With potassium dioxotetrahydroxoosmate(VI); (DHQ)2-PHAL; water; potassium carbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With osmium(VIII) oxide; (DHQ)2-DP-PHAL; Title compound not separated from byproducts;
With osmium(VIII) oxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 3h; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); water; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With osmium(VIII) oxide; sodium hydrogensulfite; bispiperazine (2d); In toluene; at -78 ℃; Yield given. Yields of byproduct given;
With osmium(VIII) oxide; 2,3-diphenyl-5,8-bis-(9-O-dihydroquinidine)pyrazino<2,3-d>pyridazine; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 30h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; further cond.: electrolytic method;
With osmium(VIII) oxide; (S)-N-(2-dimethylaminoethyl)-4,5-dihydro-3H-dinaphtho<2,1-c:1',2'-e>azepine; In tetrahydrofuran; at -78 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With MeO-PEG-modified DHQD; potassium carbonate; potassium hexacyanoferrate(III); for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With AD-mix-α; In water; tert-butyl alcohol; at 0 ℃; for 6h; Title compound not separated from byproducts;
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 28h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With phosphate buffer; oxygen; K2; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tert-butyl alcohol; at 50 ℃; under 750.06 Torr; pH=10.4; Title compound not separated from byproducts;
With air; hydroquinone 1,4-phthalazinediyl diether; K2; In water; tert-butyl alcohol; at 50 ℃; for 24h; under 15001.2 Torr; pH=10.4;
With potassium dioxotetrahydroxoosmate(VI); Benzyl phenyl selenoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium carbonate; In tert-butyl alcohol; at 20 ℃; Further Variations:; Reagents; Time; Product distribution;
With (DHQD)2PHAL; K2; oxygen; In water; tert-butyl alcohol; at 50 ℃; for 24h; under 750.06 Torr; pH=10.4; Title compound not separated from byproducts;
With potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); osmium(VIII) oxide; PEM-MC OsO4; In acetone; at 30 ℃; for 5h; Title compound not separated from byproducts;
With osmium(VIII) oxide; tetraethylammonium acetate; dihydrogen peroxide; quinidine based chiral catalyst; In water; tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
With Resin-OsO4; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 20 ℃; for 24h; Further Variations:; Reagents; 6; Product distribution;
With osmium(VIII) oxide; (QN)2PHAL; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; Title compound not separated from byproducts;
With 4-methyl-morpholine; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; dihydrogen peroxide; LDH-OsW; In tert-butyl alcohol; at 20 ℃; for 2h; Further Variations:; Reagents; Catalysts; Product distribution;
With sodium hypochlorite; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; K2; In water; tert-butyl alcohol; at 0 ℃; for 1h; pH=12.7; Further Variations:; Solvents; Reagents; Temperatures; Product distribution;
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); block copolymer-supported bis-cinchona alkaloid ligand; In water; toluene; tert-butyl alcohol; at 0 ℃; for 24h; Title compound not separated from byproducts;
With sodium chlorite; potassium osmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; sodium hydroxide; potassium chloride; In water; tert-butyl alcohol; at 0 - 1 ℃; for 1h; pH=11.8; Title compound not separated from byproducts;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium carbonate; In water; tert-butyl alcohol; at 20 ℃; for 24h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; NAP-Mg-OsO4; In water; tert-butyl alcohol; at 20 ℃; for 15h; Title compound not separated from byproducts;
With K2OsO2(OH)2; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; [C4mim]NTf2; at 20 ℃; for 24h; Further Variations:; Reagents; Product distribution;
isopropenylbenzene; With Triton X-114; potassium carbonate; potassium hexacyanoferrate(III); divinylbenzene)polystyrene resin-microencapsulated Os; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; at 30 ℃; for 24h;
With sulfuric acid; In water; at 30 ℃; for 0.166667h; Title compound not separated from byproducts;
With osmium(VIII) oxide; chiral polysiloxane-bound ligand; 4-methylmorpholine N-oxide; In acetone; at 0 - 4 ℃; for 2h; Further Variations:; Reagents; reaction time; Product distribution;
With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
With (DHQ)2-PHAL-S-(CH2)6OH on magnetic mesocellular -porous SiO2; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; In water; tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts;
isopropenylbenzene; With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); hydroquinidein 1,4-phthalazinediyl diether; In water; tert-butyl alcohol; at 20 ℃;
With ethyl vinyl ether; In water; tert-butyl alcohol; at 20 ℃; for 1h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4; In water; tert-butyl alcohol; at 20 ℃; for 12h; Title compound not separated from byproducts;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; polyaniline-supported Os; In water; acetone; acetonitrile; at 20 ℃; for 12h; Title compound not separated from byproducts;
With osmium(VIII) oxide; (DNQD)2PHAL; tetraethylammonium acetate; methyltrioxorhenium(VII); In tert-butyl alcohol; at 0 ℃; Title compound not separated from byproducts.;
With 4-methyl-morpholine; tetraethylammonium acetate; titanium silicate; silica gel*cinchona alkaloid*K2OsO4*2H2O; In water; tert-butyl alcohol; at 20 ℃; for 13h; Title compound not separated from byproducts.;
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; Triton X-114; potassium hexacyanoferrate(III); OsO4 poly[(PhO-EtO-Me-styrene)-co-styrene] microcapsules; In water; at 30 ℃; for 24h; Title compound not separated from byproducts.;
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; chiral triazine catalyst; In water; tert-butyl alcohol; at 0 ℃; for 14h; Title compound not separated from byproducts.;
With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; In water; toluene; tert-butyl alcohol; at 25 ℃; for 21h; Title compound not separated from byproducts.;
With carbon dioxide; dihydrogen peroxide; osmium(VIII) oxide; In water; acetone; at 25 ℃; under 760.051 Torr; Title compound not separated from byproducts.;
With potassium osmate(VI) dihydrate; dodecyltrimethylammonium bromide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In water; at 20 ℃; for 48h; optical yield given as %ee;
With N,N'-ethane-1,2-diyl-N,N'-[3,5-bis[3,5-bis(3,5-dimethoxybenzyloxy)benzyloxy]benzyloxy]-N,N,N',N'-tetramethylammonium dibromide; C120H134N2O28(2+)*O4Os(2-); water; 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; In acetonitrile; at 20 ℃; for 0.5h; enantioselective reaction; Inert atmosphere;
With potassium osmate(VI) dihydrate; streptavidin L124K mutant; potassium carbonate; potassium hexacyanoferrate(III); In water; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;
With seleno-L-cystine; water; dihydrogen peroxide; at 20 ℃; for 240h; Overall yield = 68 %; stereoselective reaction;
20 % ee
isopropenylbenzene; With (+)-[Rh((S,S)-Phebox-i-Pr)OAc2(H2O)]; bis(pinacol)diborane; sodium t-butanolate; In tetrahydrofuran; at 60 ℃; for 1h; Inert atmosphere;
In tetrahydrofuran; water; at 20 ℃; for 1h; enantioselective reaction; Inert atmosphere;
76 % ee
With alpha-D-glucopyranose; Escherichia coli (SST1); In Hexadecane; at 30 ℃; for 8h; pH=8; Overall yield = 24 %Chromat.; enantioselective reaction; Green chemistry; Enzymatic reaction;
46 % ee
With D-glucose; In aq. phosphate buffer; Hexadecane; at 30 ℃; for 8h; pH=8; Overall yield = 24 %Chromat.; Microbiological reaction;
46.8 % ee
2-hydroxy-2-phenyl-propionaldehyde
4361-50-6

2-hydroxy-2-phenyl-propionaldehyde

(2S)-2-phenylpropane-1,2-diol
2406-22-6

(2S)-2-phenylpropane-1,2-diol

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; water; acetonitrile; at 0 ℃; for 2h; Overall yield = 45 mg; Inert atmosphere;
50 % ee
2-hydroxy-2-phenyl-propionaldehyde
4361-50-6

2-hydroxy-2-phenyl-propionaldehyde

(2S)-2-phenylpropane-1,2-diol
2406-22-6

(2S)-2-phenylpropane-1,2-diol

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; water; acetonitrile; at 0 ℃; for 2h; Overall yield = 45 mg; Inert atmosphere;
50 % ee
(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.<sup>9,11</sup>.0<sup>2,17</sup>.0<sup>8,13</sup>]-docosane
923986-89-4

(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane

(R)-1-phenyl-1,2-ethanediol
2406-22-6,4217-66-7,87760-50-7,35638-92-7

(R)-1-phenyl-1,2-ethanediol

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol
444308-38-7

{(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol

Conditions
Conditions Yield
(1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.9,11.02,17.08,13]-docosane; With N-chloro-succinimide; silver nitrate; In water; acetonitrile; at 0 - 4 ℃;
With sodium tetrahydroborate; In water; acetonitrile; at 20 ℃; for 2h;
71%

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