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

Base Information

Chemical Name:methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside
CAS No.:352542-08-6
Molecular Formula:C₁₅H₂₁N₃O₈S
Molecular Weight:403.413
Hs Code.:

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

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

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

There total 8 articles about methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside 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:

: 67-56-1
methanol

: 352542-06-4
3-C-azido-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranose

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

: 352542-08-6
methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside

Guidance literature:: With acetyl chloride; In dichloromethane; water; at 20 ℃; for 16h; Title compound not separated from byproducts.;
DOI:10.1021/jo010299j

Reference yield:

: 114738-04-4
(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 352542-08-6
methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 7.93 g / KF; 18-crown-6; H₂O / tetrahydrofuran / 18 h / 20 °C

2: 8.75 g / Ph₃P; DEAD / tetrahydrofuran / 16.5 h / 0 - 50 °C

3: 99 percent / pyridine; CrO₃; Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

4: 74 percent / LiHMDS / tetrahydrofuran / 3 h / -78 °C

5: 87 percent / NaN₃; 18-crown-6; DBU / 1 h / 40 °C

6: 80 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 14 h / 5 °C

7: 87 percent / pyridine / 1 h / 20 °C

8: AcCl / H₂O; CH₂Cl₂ / 16 h / 20 °C

With pyridine; chromium(VI) oxide; potassium fluoride; sodium tetrahydroborate; sodium azide; 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;
DOI:10.1021/jo010299j

Reference yield:

: 43138-39-2
1,2-O-isopropylidene-β-D-arabinofuranoside

: 352542-08-6
methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 8.75 g / Ph₃P; DEAD / tetrahydrofuran / 16.5 h / 0 - 50 °C

2: 99 percent / pyridine; CrO₃; Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

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

4: 87 percent / NaN₃; 18-crown-6; DBU / 1 h / 40 °C

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

6: 87 percent / pyridine / 1 h / 20 °C

7: AcCl / H₂O; CH₂Cl₂ / 16 h / 20 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium azide; 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;
DOI:10.1021/jo010299j