(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Base Information

Chemical Name:(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
CAS No.:188871-58-1
Molecular Formula:C₁₇H₁₉NO₅
Molecular Weight:317.342
Hs Code.:

Synonyms:(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

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Chemical Property of (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

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Technology Process of (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

There total 13 articles about (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 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: 23.0%

: 188871-67-2
(2S,3R,4S,5R)-2-(6-Bromo-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

: 100-51-6,185532-71-2
benzyl alcohol

: 188871-58-1
(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Guidance literature:: With potassium hydride; In N,N-dimethyl-formamide; at 140 ℃; for 0.0833333h;
DOI:10.1016/S0040-4039(97)00197-4

Reference yield:

: 83664-33-9
2-(benzyloxy)-5-bromopyridine

: 188871-58-1
(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 47 percent / LDA / tetrahydrofuran / -78 °C

2: Et₃SiH, BF₃*Et₂O / acetonitrile / 2.5 h / 0 deg C to rt

3: TBAF / tetrahydrofuran / 0.75 h

4: 80percent aq. acetic acid / 1.5 h / Heating

With triethylsilane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0040-4039(97)00197-4

Reference yield:

: 130222-84-3
5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

: 188871-58-1
(2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 44 percent / n-BuLi / tetrahydrofuran / -100 °C

2: DMAP, TEA / acetonitrile

3: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 deg C to rt

4: 1M TBAF / tetrahydrofuran / 0.75 h

5: 80percent aq. acetic acid / 1.5 h / Heating

6: 23 percent / KH / dimethylformamide / 0.08 h / 140 °C

With triethylsilane; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)00197-4