3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

Base Information

Chemical Name:3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose
CAS No.:851050-63-0
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

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Chemical Property of 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

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Technology Process of 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

There total 1 articles about 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose 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: 91.0%

: 18439-45-7,70632-45-0,87938-30-5,18439-44-6
3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 851050-63-0
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/j.bmc.2005.01.029

Reference yield:

: 851050-63-0
3-O-benzyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hexofuranose

: 851050-69-6
1-[2,3,5-tri-O-acetyl-6-deoxy-3-C-ethynyl-β-D-allo-hexofuranosyl]-4-N-benzoylcytosine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / H₂ / Pd/C / ethyl acetate / 19 h / 20 °C

2.1: pyridinium dichromate; molecular sieves 3 Angstroem; glacial acetic acid / CH₂Cl₂ / 22 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; cyclohexane / -78 °C

3.2: 9.17 g / tetrahydrofuran; cyclohexane / 0.67 h / -78 °C

4.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5.1: pyridine; DMAP / 18 h / 20 °C

6.1: aq. trifluoroacetic acid / 3 h / 20 °C

7.1: 1.41 g / pyridine; DMAP / 94 h / 20 °C

8.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / Heating

8.2: 75 percent / trimethylsilyl triflate / acetonitrile / 21 h / Heating

With pyridine; dmap; dipyridinium dichromate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; cyclohexane; ethyl acetate; acetonitrile;
DOI:10.1016/j.bmc.2005.01.029