Locked nucleic acid 1

Base Information

• Chemical Name: Locked nucleic acid 1
• CAS No.: 206055-71-2
• Molecular Formula: C₃₂H₃₂N₂O₈
• Molecular Weight: 572.615
• DSSTox Substance ID: DTXSID101105911
• Nikkaji Number: J1.522.751F
• Mol file: 206055-71-2.mol

Synonyms:Locked nucleic acid 1;1-((1R,3R,4R,7S)-1-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;SCHEMBL5582060;DTXSID101105911;AKOS040744152;HY-111807;CS-0092583;D86086;2'alpha,4'-(Oxymethylene)-5'-O-(4,4'-dimethoxytrityl)thymidine;1-[2,5-Anhydro-4-C-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

Chemical Property of Locked nucleic acid 1

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 572.21586598
• Heavy Atom Count: 42
• Complexity: 990

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C3C(C(O2)(CO3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@H]3[C@@H]([C@@](O2)(CO3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O

Technology Process of Locked nucleic acid 1

There total 28 articles about Locked nucleic acid 1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (206055-67-6) → 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1016/S0040-4039(00)01607-5

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h

2: 90 percent / pyridine / 3 h / Ambient temperature

3: 80percent AcOH / 4 h / 90 °C

4: pyridine / 72 h / Ambient temperature

5: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

6: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

7: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

8: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

9: 93 percent / pyridine / 2 h / Ambient temperature

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol;

DOI:10.1016/S0040-4020(98)00094-5

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / pyridine / 3 h / Ambient temperature

2: 80percent AcOH / 4 h / 90 °C

3: pyridine / 72 h / Ambient temperature

4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

5: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

6: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

7: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

8: 93 percent / pyridine / 2 h / Ambient temperature

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol;

DOI:10.1016/S0040-4020(98)00094-5

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

2',3'-O-benzylidene-4'-(p-toluenesulfonyloxymethyl)uridine

2',3'-O-cyclohexylidene-4'-(p-toluenesulfonyloxymethyl)uridine