ChemicalBook > CAS DataBase List > Z-TRANS-4-HYDROXY-L-PROLINOL

Z-TRANS-4-HYDROXY-L-PROLINOL

Product Name
Z-TRANS-4-HYDROXY-L-PROLINOL
CAS No.
95687-41-5
Chemical Name
Z-TRANS-4-HYDROXY-L-PROLINOL
Synonyms
Z-Hyp-Ol;trans-N-BenzyL;-4-hydroxy-2-hydroxymethyL;1-Cbz-4-hydroxy-L-prolinol;CBZ-TRANS-4-HYDROXY-L-PROLINOL;TRANS-N-CBZ-4-HYDROXY-L-PROLINOL;1-CBZ-TRANS-4-HYDROXY-L-PROLINOL;N-CBZ-TRANS-4-HYDROXY-L-PROLINOL;Z-trans-4-Hydroxy-L-prolinol,90%;Z-TRANS-4-HYDROXY-L-PROLINOL USP/EP/BP
CBNumber
CB3504741
Molecular Formula
C13H17NO4
Formula Weight
251.28
MOL File
95687-41-5.mol
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Z-TRANS-4-HYDROXY-L-PROLINOL Property

Boiling point:
240 °C(lit.)
Density 
1.297 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.547(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
form 
clear liquid
pka
14.56±0.40(Predicted)
color 
Colorless to Light orange to Yellow
optical activity
[α]20/D 33°, c = 15 in chloroform
InChI
InChI=1S/C13H17NO4/c15-8-11-6-12(16)7-14(11)13(17)18-9-10-4-2-1-3-5-10/h1-5,11-12,15-16H,6-9H2/t11-,12+/m0/s1
InChIKey
WDEQGLDWZMIMJM-NWDGAFQWSA-N
SMILES
N1(C(OCC2=CC=CC=C2)=O)C[C@H](O)C[C@H]1CO
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Safety

Hazard Codes 
Xi
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
547085
Product name
Z-trans-4-Hydroxy-L-prolinol
Packaging
1g
Price
$165
Updated
2025/07/31
TCI Chemical
Product number
C3255
Product name
N-Carbobenzoxy-trans-4-hydroxy-L-prolinol
Purity
>95.0%(GC)
Packaging
1g
Price
$113
Updated
2025/07/31
TRC
Product number
C227708
Product name
Cbz-trans-4-hydroxy-L-Prolinol
Packaging
100mg
Price
$75
Updated
2021/12/16
Ark Pharm
Product number
AK-50270
Product name
trans-Benzyl4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Purity
97%
Packaging
250mg
Price
$24
Updated
2021/12/16
Chem-Impex
Product number
41677
Product name
N-Carbobenzoxy-trans-4-hydroxy-L-prolinol,≥95%(GC)
Purity
≥95%(GC)
Packaging
1G
Price
$182.87
Updated
2021/12/16
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Z-TRANS-4-HYDROXY-L-PROLINOL Chemical Properties,Usage,Production

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

13504-85-3

95687-41-5

N-Benzyloxycarbonyl-(4R)-hydroxy-L-proline (150 g, 0.565 mol) was used as a raw material, which was dissolved in tetrahydrofuran (1.5 L), and the borane-dimethyl sulfide complex (59.0 ml, 0.622 mol) was added dropwise slowly under stirring at 0 °C. After the dropwise addition, the reaction mixture was heated to reflux and stirred continuously for 3 hours. Subsequently, the reaction mixture was cooled to 0 °C and borane-dimethyl sulfide complex (16.1 ml, 0.170 mol) was added again and stirring was continued for 10 hours. After completion of the reaction, the reaction mixture was cooled and water (500 ml) was added slowly at 0 °C to quench the excess borane-dimethyl sulfide complex. The reaction mixture was extracted with a solvent mixture of ethyl acetate and chloroform-methanol (10:1, v/v), the organic phases were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to afford Cbz-(2S,4R)-4-hydroxyprolinol (122.06 g, 86% yield), the product was a pale yellow oil, which could be used for subsequent reactions without further purification.1H-NMR (CDCl3) δ: 1.52-1.81 (m, 3H), 2.06 (m, 1H), 3.40-3.85 and 4.04- 4.61 (m series, total 6H), 5.15 (s, 2H, ArCH2), 7.20-7.44 (m, 5H, Ar).

References

[1] Patent: EP1623975, 2006, A1. Location in patent: Page/Page column 20-21
[2] Heterocycles, 1984, vol. 22, # 12, p. 2735 - 2738
[3] Tetrahedron, 2006, vol. 62, # 10, p. 2321 - 2330
[4] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 5-8, p. 1285 - 1288
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1161 - 1174

Z-TRANS-4-HYDROXY-L-PROLINOL Preparation Products And Raw materials

Raw materials

Preparation Products

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Z-TRANS-4-HYDROXY-L-PROLINOL Suppliers

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View Lastest Price from Z-TRANS-4-HYDROXY-L-PROLINOL manufacturers

Huida Pharmaceutical Technology (Shanghai) Co., Ltd.
Product
Z-TRANS-4-HYDROXY-L-PROLINOL 95687-41-5
Price
US $0.00-0.00/kg
Min. Order
0.1kg
Purity
98%
Supply Ability
100kg
Release date
2023-03-13
Career Henan Chemical Co
Product
Z-TRANS-4-HYDROXY-L-PROLINOL 95687-41-5
Price
US $20.00/KG
Min. Order
20KG
Purity
98%
Supply Ability
20kg
Release date
2018-07-30

95687-41-5, Z-TRANS-4-HYDROXY-L-PROLINOLRelated Search:

N-Cbz-Hydroxy-L-proline Z-HYP-OME Z-HYP(TBU)-OH Z-Hyp(tBu)-OMe L-(+)-Prolinol 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER AKOS 335 Z-TRANS-4-HYDROXY-L-PROLINOL N-BENZYLOXYCARBONYL-5-ANTI-BROMO-6-ANTI-ACETOXY-3-ENDO-(HYDROXYMETHYL)-2-AZABICYCLO[2.1.1]HEXANE L-ZHPROMSME

  • (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)-pyrrolidine
  • (3R,5S)-1-Cbz-5-(hydroxymethyl)-3-pyrrolidinol
  • Trans-N-benzyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine
  • Z-Hyp-Ol
  • Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
  • 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylic acid
  • trans-Benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
  • N-Carbobenzoxy-trans-4-hydroxy-L-prolinol
  • 1-Pyrrolidinecarboxylicacid, 4-hydroxy-2-(hydroxymethyl)-, phenylmethyl ester, (2S,4R)-
  • TRANS-N-CBZ-4-HYDROXY-L-PROLINOL
  • CBZ-TRANS-4-HYDROXY-L-PROLINOL
  • (2S,4R)4-Hydroxy-2-(hydroxymethyl)pyrrolidine, N-CBZ protected
  • 1-CBZ-TRANS-4-HYDROXY-L-PROLINOL
  • N-CBZ-TRANS-4-HYDROXY-L-PROLINOL
  • trans-N-BenzyL
  • -4-hydroxy-2-hydroxymethyL
  • (2S,4R)-4-Hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylic Acid Benzyl Ester
  • N-Benzyloxycarbonyl-trans-4-hydroxy-L-prolinol
  • Z-TRANS-4-HYDROXY-L-PROLINOL USP/EP/BP
  • 1-Cbz-4-hydroxy-L-prolinol
  • Z-trans-4-Hydroxy-L-prolinol,90%
  • Z-<i>trans</i>-4-Hydroxy-<sc>L</sc>-prolinol
  • 95687-41-5
  • Amino Alcohols
  • Peptide Synthesis
  • Amino Acid Derivatives
  • Amino Acid Derivatives