100836-85-9

Basic information

• Product Name: (R)-(+)-2-BENZYLOXYPROPIONIC ACID
• Synonyms: O-BENZYL-D-LACTIC ACID;(R)-(+)-2-BENZYLOXYPROPIONIC ACID;(2R)-2-(Benzyloxy)propionic acid;(R)-2-(Benzyloxy)propanoic acid;(R)-(+)-2-(Benzyloxy)propionic acid[>=97.0% (HPLC)];(R)-(+)-O-Benzyllactic acid;Propanoic acid, 2-(phenylMethoxy)-, (2R)-
• CAS NO: 100836-85-9
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: -0
• Mol File: 100836-85-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 52-55 °C
• Boiling Point: 328.2°Cat760mmHg
• Flash Point: 130.4°C
• Appearance: /
• Density: 1.150
• Vapor Pressure: 7.79E-05mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.57±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 4675524
• CAS DataBase Reference: (R)-(+)-2-BENZYLOXYPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-BENZYLOXYPROPIONIC ACID(100836-85-9)
• EPA Substance Registry System: (R)-(+)-2-BENZYLOXYPROPIONIC ACID(100836-85-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 100836-85-9(Hazardous Substances Data)

Usage

Uses

(R)-(+)-2-Benzyloxypropionic acid is used as a pharmaceutical intermediate.

InChI:InChI=1/C10H12O3/c1-8(10(11)12)13-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)/t8-/m1/s1

Synthetic route

1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl 2-(benzyloxy)propionate → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With lithium hydroxide; water In tetrahydrofuran	98%

(R)-2-(benzyloxy) methyl propionate (115458-99-6) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 0.5h;	94%
With sodium hydroxide In methanol	89%
With methanol; lithium hydroxide at 20℃; for 5h;	78%

C16H28O3Si2 → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2.6-dimethylphenol; C32H12BF24(1-)*C44H30N2O2P(1+) In toluene at -40℃; for 24h; Inert atmosphere; enantioselective reaction;	86%

(S)-2-chloropropanoic acid (29617-66-1) + benzyl alcohol (100-51-6) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Stage #1: benzyl alcohol With sodium at 80 - 90℃; for 2h; Stage #2: (S)-2-chloropropanoic acid at 55℃; for 3h; Stage #3: With hydrogenchloride In tert-butyl methyl ether; water pH=1.5 - 6.5;	84%

(2S,4R)-3-[(R)-2-benzyloxypropanoyl]-2-trifluoromethyl-4-phenyl-1,3-oxazolidine (1220352-28-2) → (R)-2-benzyloxypropionic acid (100836-85-9) + (2S,4R)-2-trifluoromethyl-4-phenyl-1,3-oxazolidine (203176-56-1)

Conditions	Yield
Stage #1: (2S,4R)-3-[(R)-2-benzyloxypropanoyl]-2-trifluoromethyl-4-phenyl-1,3-oxazolidine With lithium aluminium tetrahydride In diethyl ether at -10℃; for 2h; Inert atmosphere; Stage #2: With water; sodium hydroxide In diethyl ether Inert atmosphere; Further stages;	A 82% B 57%

C24H28N2O3 → trans-3-benzyl-3,7-diazabicyclo[4.3.0]nonan-8-one + 2-(1-benzyl-4-(2-(benzyloxy)propanamido)piperidin-3-yl)acetic acid hydrochloride + (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With water; dihydrogen peroxide; lithium hydroxide In tetrahydrofuran at 0℃; for 1.5h;	A 7% B n/a C n/a

2-(benzyloxy)propanoic acid (33106-32-0, 74431-49-5, 100836-85-9, 6625-78-1) → 2-benzyloxypropanol (33106-26-2, 33106-64-8, 70448-03-2, 87037-69-2) + (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Yield given. Yields of byproduct given;

[(4R,5S)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane (105544-95-4) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multistep reaction;
Multi-step reaction with 4 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C 2: acetic acid / H2O / 10 h / 80 °C 3: NaIO4 / acetone; H2O / 3 h / 24 °C 4: CrO3 / acetic acid; pyridine / 3 h / 23 °C View Scheme

(2S,3R)-3-Benzyloxy-butane-1,2-diol (87604-62-4) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 2h; Ambient temperature; Yield given;

N-<(R)-α-benzyloxypropionyl>-cyclo-(β-alanylprolyl) (82939-03-5) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With hydrogenchloride In methanol for 5h; Ambient temperature;

L-alanin (56-41-7) + benzyl alcohol (100-51-6) → (R)-2-benzyloxypropionic acid (100836-85-9) + (S)-2-(benzyloxy)propanoic acid (33106-32-0)

Conditions	Yield
With magnesium sulfate; isopentyl nitrite for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

D-Alanine (338-69-2) + benzyl alcohol (100-51-6) → (R)-2-benzyloxypropionic acid (100836-85-9) + (S)-2-(benzyloxy)propanoic acid (33106-32-0)

Conditions	Yield
With magnesium sulfate; isopentyl nitrite for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

N-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)-pyrrolidine + methyl iodide (74-88-4) → (R)-2-benzyloxypropionic acid (100836-85-9) + (S)-2-(benzyloxy)propanoic acid (33106-32-0)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(R)-2-benzyloxypropanal (53346-05-7, 41954-96-5, 81445-44-5, 81445-45-6) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
With chromium(VI) oxide In pyridine; acetic acid at 23℃; for 3h; Yield given;

(2R,4aR,7R,8aR)-2-((R)-1-Benzyloxy-ethyl)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalene (191982-83-9) → (R)-2-benzyloxypropionic acid (100836-85-9) + (3aR,6R,7aR)-3,3,6-Trimethyl-hexahydro-benzo[d][1,2]oxathiole 2-oxide (79563-63-6)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; 2-methyl-but-2-ene; silver nitrate 1) aq. CH3CN, -4 deg C, 10 min, 2) tBuOH, r.t., 20 h; Yield given. Multistep reaction;

(S)-3-(2-Benzyloxy-propionyl)-4-isopropyl-1-phenyl-imidazolidin-2-one → (R)-2-benzyloxypropionic acid (100836-85-9) + (S)-2-(benzyloxy)propanoic acid (33106-32-0)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water Title compound not separated from byproducts;

benzyloxyacetic acid (30379-55-6) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 78 percent / DCC; DMAP 2.1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 2.2: 80 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 3.1: 98 percent / LiOH; H2O / tetrahydrofuran View Scheme

1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate (341489-97-2) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 1.2: 80 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 2.1: 98 percent / LiOH; H2O / tetrahydrofuran View Scheme

benzyl bromide (100-39-0) + potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide> → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / NaH / 1,2-dimethoxy-ethane 2: 89 percent / 2N NaOH / methanol View Scheme
Multi-step reaction with 2 steps 1: 95 percent / NaH, Bu4NSO4H / tetrahydrofuran / 0.67 h / Heating 2: 1) NCS, AgNO3, 2) 2-methyl-2-butene, NaClO2, 1.6 M NaH2PO4*H2O / 1) aq. CH3CN, -4 deg C, 10 min, 2) tBuOH, r.t., 20 h View Scheme

(2R,3R,4R)-4-Benzyloxy-pentane-1,2,3-triol → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaIO4 / acetone; H2O / 3 h / 24 °C 2: CrO3 / acetic acid; pyridine / 3 h / 23 °C View Scheme

[(4R,5S)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid / H2O / 10 h / 80 °C 2: NaIO4 / acetone; H2O / 3 h / 24 °C 3: CrO3 / acetic acid; pyridine / 3 h / 23 °C View Scheme

(+)-R-2-benzyloxypropionic acid chloride (82977-93-3) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.70 g / pyridine / dioxane / 15 h / 80 °C 2: aq. HCl / methanol / 5 h / Ambient temperature View Scheme

ethyl 2-benzyloxypropionate (2040-44-0) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent KOH / 2 h / Heating View Scheme

benzyl alcohol (100-51-6) + BeCl2 → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 4.5 g / Na / 5 h / Heating 2: 60 percent KOH / 2 h / Heating View Scheme

benzoic acid (65-85-0) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ti(O-iPr)4 / CH2Cl2 / 0.5 h / Ambient temperature 2: 2percent RuCl3*5H2O, NaIO4 / acetonitrile; CCl4; H2O / 2 h / Ambient temperature View Scheme

2-(benzyloxy)propanoic acid (33106-32-0, 74431-49-5, 100836-85-9, 6625-78-1) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 20 °C 2: 2.6-dimethylphenol; C32H12BF24(1-)*C44H30N2O2P(1+); 2,6-di-tert-butyl-pyridine / toluene / 24 h / -40 °C / Inert atmosphere View Scheme

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid 2: lithium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid / dichloromethane; hexane / 20 °C 2: lithium hydroxide / tetrahydrofuran / 20 °C View Scheme

benzyl bromide (100-39-0) → (R)-2-benzyloxypropionic acid (100836-85-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 16 h / 75 °C 2: potassium hydroxide / water; methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: silver(l) oxide / dichloromethane / 48 h / 20 °C / Inert atmosphere 2: potassium hydroxide; water / ethanol / 0.5 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: silver(l) oxide / tert-butyl methyl ether / 20 h / 20 °C 2: lithium hydroxide; methanol / 5 h / 20 °C View Scheme

(R)-2-benzyloxypropionic acid (100836-85-9) → (R)-2-(benzyloxy)propan-1-ol (87037-69-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18h;	100%

benzylamine hydrochloride (3287-99-8, 39110-74-2) + (R)-2-benzyloxypropionic acid (100836-85-9) → (R)-N-benzyl-2-(benzyloxy)propanamide

Conditions	Yield
Stage #1: benzylamine hydrochloride; (R)-2-benzyloxypropionic acid With dmap; triethylamine In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: With 9,9-dichloro-9-silafluorene In tetrahydrofuran at 20 - 60℃; Inert atmosphere;	99%

L-proline tert-butyl ester hydrochloride (5497-76-7) + (R)-2-benzyloxypropionic acid (100836-85-9) → (S)-1-((R)-2-Benzyloxy-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (203783-50-0)

Conditions	Yield
With benzotriazol-1-ol; dacarbazine In tetrahydrofuran	96%

(R)-2-benzyloxypropionic acid (100836-85-9) → (+)-R-2-benzyloxypropionic acid chloride (82977-93-3)

Conditions	Yield
With oxalyl dichloride at 20 - 55℃; for 2.25h;	94.9%
With thionyl chloride In chloroform at 60℃; for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 1 - 15℃; for 0.5h;

(R)-2-benzyloxypropionic acid (100836-85-9) + 2-(pyridin-2-yl)isopropyl amine (52568-28-2) → C18H22N2O2

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	92%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	92%

C20H38N2O5 (1126974-97-7) + (R)-2-benzyloxypropionic acid (100836-85-9) → C30H48N2O7 (1126975-14-1)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice; Inert atmosphere;	91%

C20H38N2O5 (1126975-03-8) + (R)-2-benzyloxypropionic acid (100836-85-9) → C30H48N2O7 (1126975-09-4)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;	87%

(R)-2-benzyloxypropionic acid (100836-85-9) + L-phenylalanyl-α-azaproline tert-butyl ester (159174-60-4) → N-<(R)-2-benzyloxypropionyl>-L-phenylalanyl-α-azaproline tert-butyl ester (159174-59-1)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran; methanol 1.) 0 deg C, 4 h, 2.) 5 deg C, 16 h;	86%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (R)-2-benzyloxypropionic acid (100836-85-9) → C17H19NO3

Conditions	Yield
Stage #1: (R)-2-benzyloxypropionic acid With pivaloyl chloride; triethylamine at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride at 20℃; for 16h; Inert atmosphere;	85%

(R)-2-benzyloxypropionic acid (100836-85-9) + 1-benzoyl-3-(R)-methylpiperazine (357263-39-9) → (2R)-1-[(2R)-4-Benzoyl-2-methyl-piperazin-1-yl]-2-benzyloxy-propan-1-one (845655-45-0)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 21h; Heating / reflux;	81%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 21h; Heating / reflux;	81%

4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)-pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)-benzonitrile (1034414-82-8) + (R)-2-benzyloxypropionic acid (100836-85-9) → (R)-2-(benzyloxy)-N'-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)propanehydrazide (1034414-94-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h;	76%

4-(methylsulfonyl)benzonitrile (22821-76-7) + (R)-2-benzyloxypropionic acid (100836-85-9) → (±)-2-(benzyloxy)propanenitrile (34097-57-9)

Conditions	Yield
With riboflavin-2',3',4',5'-tetra-acetate In acetonitrile at 25℃; for 23h; Inert atmosphere; Irradiation; Sealed tube;	70%

(R)-2-benzyloxypropionic acid (100836-85-9) + thiosemicarbazide (79-19-6) → 5-[1-(benzyloxy)ethyl]-1,3,4-thiadiazol-2-amine

Conditions	Yield
With trichlorophosphate In 1,4-dioxane at 80℃; for 2h;	65%

(R)-2-benzyloxypropionic acid (100836-85-9) + benzylamine (100-46-9) → (R)-N-benzyl-2-(benzyloxy)propanamide

Conditions	Yield
With diphenylsilane In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube; Green chemistry;	65%

L-Lactic acid (79-33-4) + (R)-2-benzyloxypropionic acid (100836-85-9) + Zithromax(R) (83905-01-5, 92470-27-4) → (2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadecan-11-yl)oxy)-6-metkyltetrahydro-2H-pyran-3-yl (S)-2-(((R)-2-(benzyloxy)propanoyl)oxy)propanoate

Conditions

Yield

Stage #1: (R)-2-benzyloxypropionic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: L-Lactic acid In dichloromethane at 20℃; for 0.5h; Stage #3: Zithromax(R) With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;

64%

1-(5-fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone (1300582-07-3) + (R)-2-benzyloxypropionic acid (100836-85-9) → (R)-2-(1-(benzyloxy)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

Conditions	Yield
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	63%
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	63%
With triethylamine; HATU In dichloromethane at 20℃; for 24h;	63%
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 25 - 28℃; for 24h;	60%
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-(3-fluorophenyl)ethanone; (R)-2-benzyloxypropionic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 25 - 28℃; for 24h;	60%

benzyl 4-[(2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanamido]-5-phenylpentanoate + (R)-2-benzyloxypropionic acid (100836-85-9) → benzyl 4-(3-{[2-(benzyloxy)propanoyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}butanamido)-5-phenylpentanoate

Conditions	Yield
Stage #1: benzyl 4-[(2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanamido]-5-phenylpentanoate; (R)-2-benzyloxypropionic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at -20℃; for 0.25h; Inert atmosphere; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;	63%

(+)-tert-butyl D-lactate (13650-70-9) + (R)-2-benzyloxypropionic acid (100836-85-9) → 2-{2-(benzyloxy)-propanoyloxy}propanoic acid tert-butyl ester

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 48h; Reflux;	60%

D-lactic acid t-butyl ester (68166-83-6) + (R)-2-benzyloxypropionic acid (100836-85-9) → 2-{2-(benzyloxy)-propanoyloxy}propanoic acid tert-butyl ester

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 48h; Reflux;	60%

benzyl 4-(2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanamido)butanoate + (R)-2-benzyloxypropionic acid (100836-85-9) → benzyl 4-[(2S,3R)-3-{[(2R)-2-(benzyloxy)propanoyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}butanamido]butanoate

Conditions	Yield
Stage #1: benzyl 4-(2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanamido)butanoate; (R)-2-benzyloxypropionic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at -20℃; for 0.25h; Inert atmosphere; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;	58%

2-(3-fluorophenyl)-1-(2-hydroxyphenyl)ethanone (1300581-93-4) + (R)-2-benzyloxypropionic acid (100836-85-9) → (R)-2-(1-(benzyloxy)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one

Conditions	Yield
Stage #1: 2-(3-fluorophenyl)-1-(2-hydroxyphenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	55%
Stage #1: 2-(3-fluorophenyl)-1-(2-hydroxyphenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	55%
Stage #1: 2-(3-fluorophenyl)-1-(2-hydroxyphenyl)ethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	55%
With triethylamine; HATU In dichloromethane at 20℃; for 24h;	55%

2-(phenylsulfonyl)benzo[d]thiazole (64345-00-2) + (R)-2-benzyloxypropionic acid (100836-85-9) → 2-(1-(benzyloxy)ethyl)benzo[d]thiazole

Conditions	Yield
With riboflavin tetraacetate In acetonitrile at 25℃; Sealed tube; Inert atmosphere; Irradiation;	40%

butyl 2-((phenylsulfonyl)methyl)acrylate + (R)-2-benzyloxypropionic acid (100836-85-9) → butyl 4-(benzyloxy)-2-methylenepentanoate

Conditions	Yield
With riboflavin tetraacetate In acetonitrile at 25℃; for 22h; Inert atmosphere; Irradiation; Sealed tube;	35%

(R)-2-benzyloxypropionic acid (100836-85-9) + Zithromax(R) (83905-01-5, 92470-27-4) → (2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadecan-11-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl (R)-2-(benzyloxy)propanoate

Conditions	Yield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 19h;	33%

1-(5-fluoro-2-hydroxyphenyl)-2-phenylethanone (343-59-9) + (R)-2-benzyloxypropionic acid (100836-85-9) → (R)-2-(1-(benzyloxy)ethyl)-6-fluoro-3-phenyl-4H-chromen-4-one

Conditions	Yield
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-phenylethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	19%
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)-2-phenylethanone; (R)-2-benzyloxypropionic acid With HATU In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 24h;	19%
With triethylamine; HATU In dichloromethane at 20℃; for 24h;	19%

Upstream product

• 53346-03-5 2-benzyloxypropionic acid methyl ester 
• 105544-95-4 [(4R,5S)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane 
• 2040-44-0 ethyl 2-benzyloxypropionate 
• 29617-66-1 (S)-2-chloropropanoic acid 
• 100-51-6 benzyl alcohol 
• 1220352-28-2 (2S,4R)-3-[(R)-2-benzyloxypropanoyl]-2-trifluoromethyl-4-phenyl-1,3-oxazolidine 
• 598-72-1 2-Bromopropionic acid 
• 20194-18-7 sodium phenyl-methanolate 
• 74-83-9 methyl bromide 
• 30379-55-6 benzyloxyacetic acid 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 849585-22-4 LACTIC ACID 
• 100-39-0 benzyl bromide 
• 33106-32-0 2-(benzyloxy)propanoic acid 

Downstream Products

• 33106-64-8 (S)-2-(benzyloxy)propan-1-ol 
• 87037-69-2 (R)-2-(benzyloxy)propan-1-ol 
• 56972-68-0 2-benzyloxy-propionyl chloride 
• 33106-26-2 2-benzyloxypropanol 
• 100-51-6 benzyl alcohol 
• 53346-03-5 2-benzyloxypropionic acid methyl ester 
• 322477-67-8 2-benzyloxypropionic acid anhydride 
• 87841-71-2 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-benzyloxy-propyl ester 
• 87841-70-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-2-benzyloxy-propyl ester 
• 132103-71-0 (R,S)-(2)-Benzyloxy-<1,1-²H2>propanol 
• 135364-13-5 (R,S)-2-Benzyloxy-1-brom-<1,1-²H2>propan 
• 135364-15-7 (R,S)-Diethyl-(2-benzyloxy-<1,1-²H2>propyl)phosphonat 
• 845655-45-0 (2R)-1-[(2R)-4-Benzoyl-2-methyl-piperazin-1-yl]-2-benzyloxy-propan-1-one 
• 1220352-34-0 (2R)-2-(benzyloxy)-N-((S)-1-phenylethyl)propanamide 

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