1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine

Base Information

• Chemical Name: 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine
• CAS No.: 352542-10-0
• Molecular Formula: C₁₉H₂₃N₅O₉S
• Molecular Weight: 497.486

Synonyms:1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine

Chemical Property of 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine

There total 9 articles about 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine 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: 32.0%

thymin (65-71-4,28806-14-6,691841-57-3) + methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside (352542-08-6) → 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine (352542-10-0) + 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-α-D-arabinofuranosyl)thymine (352542-12-2)

Guidance literature:

thymin; methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside; With chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 60 ℃; for 1h;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 70 ℃; for 48h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo010299j

Reference yield:

1,2-O-isopropylidene-β-D-arabinofuranoside (43138-39-2) → 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine (352542-10-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 8.75 g / Ph₃P; DEAD / tetrahydrofuran / 16.5 h / 0 - 50 °C

2.1: 99 percent / pyridine; CrO₃; Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 74 percent / LiHMDS / tetrahydrofuran / 3 h / -78 °C

4.1: 87 percent / NaN₃; 18-crown-6; DBU / 1 h / 40 °C

5.1: 80 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 14 h / 5 °C

6.1: 87 percent / pyridine / 1 h / 20 °C

7.1: AcCl / H₂O; CH₂Cl₂ / 16 h / 20 °C

8.1: N,O-bis(trimethylsilyl)acetamide; TMS-Cl / acetonitrile / 1 h / 60 °C

8.2: TMS-OTf / acetonitrile / 48 h / 70 °C

8.3: 32 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo010299j

Reference yield:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4) → 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine (352542-10-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 7.93 g / KF; 18-crown-6; H₂O / tetrahydrofuran / 18 h / 20 °C

2.1: 8.75 g / Ph₃P; DEAD / tetrahydrofuran / 16.5 h / 0 - 50 °C

3.1: 99 percent / pyridine; CrO₃; Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 74 percent / LiHMDS / tetrahydrofuran / 3 h / -78 °C

5.1: 87 percent / NaN₃; 18-crown-6; DBU / 1 h / 40 °C

6.1: 80 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 14 h / 5 °C

7.1: 87 percent / pyridine / 1 h / 20 °C

8.1: AcCl / H₂O; CH₂Cl₂ / 16 h / 20 °C

9.1: N,O-bis(trimethylsilyl)acetamide; TMS-Cl / acetonitrile / 1 h / 60 °C

9.2: TMS-OTf / acetonitrile / 48 h / 70 °C

9.3: 32 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; chromium(VI) oxide; potassium fluoride; sodium tetrahydroborate; chloro-trimethyl-silane; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; water; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo010299j

upstream raw materials:

thymin

methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside

1,2-O-isopropylidene-β-D-arabinofuranoside

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

(1R,2S,4R,5S)-1-azido-2-(p-methoxyphenoxy)methyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane

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