(E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose

Base Information

• Chemical Name: (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose
• CAS No.: 138459-02-6
• Molecular Formula: C₄₉H₇₄O₉Si₂
• Molecular Weight: 863.292
• Mol file: 138459-02-6.mol

Synonyms:

Chemical Property of (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose

There total 14 articles about (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-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:

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose (138459-01-5) + Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (138459-00-4) → (Z)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose (138459-02-6,138514-61-1) + (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose (138459-02-6,138514-61-1)

Guidance literature:

With potassium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00029a024

Reference yield:

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose (138459-01-5) + Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (138459-00-4) → (Z)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose (138459-02-6,138514-61-1) + (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose (138459-02-6,138514-61-1)

Guidance literature:

With potassium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00029a024

Reference yield:

D-Arabinose (10323-20-3) → (Z)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose (138459-02-6,138514-61-1)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 89 percent / imidazole / dimethylformamide / 18 h / 25 °C

4: 97 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

5: KH / tetrahydrofuran / 1.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; potassium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00029a024

upstream raw materials:

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose

Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

D-Arabinose

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose diethyl dithioacetal