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Chemical Structure| 6027-21-0 Chemical Structure| 6027-21-0
Chemical Structure| 6027-21-0

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CAS No.: 6027-21-0

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H-D-HoSer-OH is a hydroxyserine derivative, maintaining serine activity in polypeptide synthesis and playing an important role in cellular function regulation.

Synonyms: H-D-Homoser-OH

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Product Details of H-D-HoSer-OH

CAS No. :6027-21-0
Formula : C4H9NO3
M.W : 119.12
SMILES Code : O=C(O)[C@H](N)CCO
Synonyms :
H-D-Homoser-OH
MDL No. :MFCD00077786
InChI Key :UKAUYVFTDYCKQA-GSVOUGTGSA-N
Pubchem ID :2724170

Safety of H-D-HoSer-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-D-HoSer-OH

* 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 [ 6027-21-0 ]
  • Downstream synthetic route of [ 6027-21-0 ]

[ 6027-21-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 348-67-4 ]
  • [ 6027-21-0 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With methyl iodide In methanol; water at 20℃; for 48 h;
Stage #2: for 15 h; Reflux		 According to a literature procedure,19D-methionine (1) (25.0 g,167.5 mmol, 1 equiv) was suspended in H2O/MeOH (466 mL/66 mL), and methyl iodide (25.2 mL, 405.4 mmol, 2.4 equiv) wasadded. The resulting suspension was stirred vigorously at roomtemperature for 48 h. Then the volume of the reaction mixturewas reduced to one-third by evaporation under vacuo and alongwith this, excess of methyl iodide was also removed. Water(155 mL) was added to the remaining reaction mixture followedby NaHCO3 (14.07 g, 167.5 mmol, 1 equiv). The resulting solutionwas refluxed for 15 h and cooled to room temperature. Solventwas removed under vacuo to yield thick syrup. This was dissolvedin water (45 mL) with heating. Addition of acetone (90 mL) followedby ethanol (1000 mL) resulted in the precipitation of a whitesolid, which was filtered and dried under vacuum to give 2 aswhite solid. Yield: 9.9 g (83 mmol, 50percent). Mp 202 C. 1H NMR(300 MHz, D2O): d = 1.92–1.78 (m, 1H, 3-CH), 2.09–2.92 (m, 1H,3-CH), 3.65–3.58 (m, 2H, 4-CH2), 3.68 (dd, 3JH,H = 4.8, 3JH,H = 7.5 Hz,1H, 2-CH). 13C NMR (75 MHz, D2O): d = 32.1 (s, 3-C), 53.3 (s, 2-C),58.5 (s, 4-C), 174.5 (s, 1-C). HRMS (ESI+, MeOH): m/z = 142.0468[M+Na]+ calcd for C4H9NO3Na+ 142.0475.
References: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5168 - 5181.
[2] Tetrahedron, 1988, vol. 44, # 2, p. 637 - 642.
  • 2
  • [ 3493-10-5 ]
  • [ 6027-21-0 ]
References: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 7917 - 7927.
  • 3
  • [ 206194-18-5 ]
  • [ 6027-21-0 ]
References: [1] Tetrahedron, 2002, vol. 58, # 47, p. 9621 - 9628.
  • 4
  • [ 104347-13-9 ]
  • [ 6027-21-0 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 12, p. 2322 - 2325.
  • 5
  • [ 50-00-0 ]
  • [ 338-69-2 ]
  • [ 6027-21-0 ]
References: [1] ACS Catalysis, 2017, vol. 7, # 3, p. 1707 - 1711.
  • 6
  • [ 328-50-7 ]
  • [ 1927-25-9 ]
  • [ 6027-21-0 ]
  • [ 6893-26-1 ]
  • [ 56-86-0 ]
References: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 17, p. 3505 - 3509.
  • 7
  • [ 51744-82-2 ]
  • [ 6027-21-0 ]
References: [1] Archives of Biochemistry, 1953, vol. 42, p. 212,214.
  • 8
  • [ 41088-89-5 ]
  • [ 6027-21-0 ]
  • [ 110045-70-0 ]
References: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2004, vol. 59, # 4, p. 451 - 467.
 

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