3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

Base Information

Chemical Name:3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose
CAS No.:352541-87-8
Molecular Formula:C₂₆H₃₅N₃O₇SSi
Molecular Weight:561.731
Hs Code.:

Synonyms:3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

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Chemical Property of 3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

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Technology Process of 3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

There total 5 articles about 3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose 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: 77.0%

: 124-63-0
methanesulfonyl chloride

: 352541-86-7
3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-hydroxymethyl-β-D-arabinofuranose

: 352541-87-8
3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

Guidance literature:: With pyridine; at 20 ℃; for 1h;
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

: 352541-87-8
3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / CrO₃; pyridine; Ac₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 54 percent / LiHMDS / tetrahydrofuran / 3 h / -78 °C

3: 68 percent / NaN₃; 18-crown-6; DBU / 1 h / 50 °C

4: 66 percent / NaBH₄ / aq. ethanol / 12 h / 5 °C

5: 77 percent / pyridine / 1 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; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo010299j

Reference yield:

: 172751-32-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

: 352541-87-8
3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 54 percent / LiHMDS / tetrahydrofuran / 3 h / -78 °C

2: 68 percent / NaN₃; 18-crown-6; DBU / 1 h / 50 °C

3: 66 percent / NaBH₄ / aq. ethanol / 12 h / 5 °C

4: 77 percent / pyridine / 1 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; 18-crown-6 ether; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;
DOI:10.1021/jo010299j