(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
• Mol file: 188871-58-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(2S,3R,4S,5R)-2-(6-Bromo-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (188871-67-2) + benzyl alcohol (100-51-6,185532-71-2) → (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (188871-58-1)

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:

2-(benzyloxy)-5-bromopyridine (83664-33-9) → (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (188871-58-1)

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:

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → (2S,3R,4S,5R)-2-(6-Benzyloxy-pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (188871-58-1)

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

upstream raw materials:

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

benzyl alcohol

2,5-dibromopyridine

2-(benzyloxy)-5-bromopyridine