6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

Base Information

Chemical Name:6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose
CAS No.:676342-57-7
Molecular Formula:C₂₆H₃₆O₆Si
Molecular Weight:472.654
Hs Code.:

Synonyms:6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

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Chemical Property of 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

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Technology Process of 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

There total 12 articles about 6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose 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%

: 32166-85-1
(S)-1-((3aR,5R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 676342-57-7
6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1002/chem.200305096

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 676342-57-7
6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: CrO₃; Ac₂O; pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: 4.49 g / NaBH₄ / methanol

3: NaH / tetrahydrofuran / 20 °C

4: 1.76 g / acetic acid; water / 48 h

5: 87 percent / triethylamine; DMAP / CH₂Cl₂ / 30 h / 20 °C

6: PPh₃; DIAD / toluene / 144 h / 20 °C

7: 848 mg / K₂CO₃ / methanol / 0.33 h

With pyridine; chromium(VI) oxide; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; water; acetic anhydride; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 6: Mitsunobu reaction;
DOI:10.1021/jo070520d

Reference yield:

: 81562-09-6
6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

: 676342-57-7
6-O-tert-butyldiphenylsilyl-1,2-di-O-isopropylidene-3-O-methyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: aq. AcOH / 9 h / 40 °C

2.1: 95 mg / camphorsulfonic acid / acetone / 0.08 h / 20 °C

3.1: 98 percent / pyridinium dichromate; Ac₂O / CH₂Cl₂ / 2 h / Heating

4.1: 92 percent / NaBH₄ / aq. ethanol / 3 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / cooling

5.2: 93 percent / tetrahydrofuran

6.1: 92 percent / aq. AcOH / 10 h / 40 °C

7.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; sodium tetrahydroborate; dipyridinium dichromate; camphor-10-sulfonic acid; acetic anhydride; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; acetone;
DOI:10.1002/chem.200305096