(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

Base Information

Chemical Name:(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose
CAS No.:138459-10-6
Molecular Formula:C₂₆H₃₆O₅Si
Molecular Weight:456.654
Hs Code.:

Synonyms:(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

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Chemical Property of (E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

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Technology Process of (E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

There total 6 articles about (E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose 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: 99.0%

: 138458-97-6
(E)-5-O-Acetyl-6-O-(tert-butyldiphenylsilyl)-1-formyl-3,4-O-isopropylidene-1,2-dideoxy-D-gluco-hex-1-enose

: 138459-10-6
(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 0.416667h;
DOI:10.1021/jo00029a024

Reference yield:

: 10323-20-3
D-Arabinose

: 138459-10-6
(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

Guidance literature:: Multi-step reaction with 6 steps

1: 1) conc. HCl / 1) 30 min, 2) 2 h

2: 86 percent / p-TsOH / methanol; H₂O / 36 h / -10 °C

3: 1) imidazole, 2) pyridine / 1) DMF, 25 deg C, 4 h, 2) 60 deg C, 2 d

4: 95 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

5: 12 percent / tetrahydrofuran / 12 h / 25 °C

6: 99 percent / DIBAL-H / tetrahydrofuran; toluene / 0.42 h / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; toluene; acetonitrile;
DOI:10.1021/jo00029a024

Reference yield:

: 138458-96-5
4-O-Acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-arabinose

: 138459-10-6
(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

Guidance literature:: Multi-step reaction with 2 steps

1: 12 percent / tetrahydrofuran / 12 h / 25 °C

2: 99 percent / DIBAL-H / tetrahydrofuran; toluene / 0.42 h / -78 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1021/jo00029a024