N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine

Base Information

• Chemical Name: N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine
• CAS No.: 141684-88-0
• Molecular Formula: C₂₇H₃₁N₅O₂Si
• Molecular Weight: 485.661

Synonyms:N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine

Chemical Property of N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine

Chemical Property:

Purity/Quality:

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MSDS Files:

SDS file from LookChem

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Technology Process of N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine

There total 9 articles about N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine 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: 96.5%

N6-methyl-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>adenine (141684-83-5) → N6-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine (141684-88-0)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00040a031

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → N6-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine (141684-88-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min

3: tetrahydrofuran / -78 °C

4: DIBAL-H / toluene / 2 h / -78 °C

5: 96 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h

7: 85.5 percent / methanol; H₂O / 18 h / 85 °C

8: 96.5 percent / 30percent aq. H₂O₂, pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00040a031

Reference yield:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol → N6-methyl-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl>adenine (141684-88-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

2: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h

3: 85.5 percent / methanol; H₂O / 18 h / 85 °C

4: 96.5 percent / 30percent aq. H₂O₂, pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; water;

DOI:10.1021/jo00040a031

upstream raw materials:

N⁶-methyl-9-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>adenine

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

Downstream raw materials:

N⁶-methyl-9-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine

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