((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol

Base Information

• Chemical Name: ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol
• CAS No.: 185627-33-2
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 185627-33-2.mol

Synonyms:

Chemical Property of ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol

There total 13 articles about ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol 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:

dimethyl 2,3-O-benzylidene-L-tartrate (38270-72-3) → ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol (185627-33-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / AlCl₃, LiAlH₄ / diethyl ether; CH₂Cl₂ / 1.) RT, 1 h, 2.) reflux, 3 h

2: 94 percent / TsOH / 12 h / Ambient temperature

3: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

4: methanol / 20 h

5: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

6: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

7: 93 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

8: DIBAL-H / toluene / 3.5 h / -78 °C

9: HCl / 20 h / Ambient temperature

10: n-Bu₄NF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; aluminium trichloride; dimethylsulfide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0957-4166(96)00424-7

Reference yield:

benzaldehyde (100-52-7) → ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol (185627-33-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 91 percent / TsOH*H₂O / benzene / 45 h / Heating

2: 93 percent / AlCl₃, LiAlH₄ / diethyl ether; CH₂Cl₂ / 1.) RT, 1 h, 2.) reflux, 3 h

3: 94 percent / TsOH / 12 h / Ambient temperature

4: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

5: methanol / 20 h

6: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

7: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

8: 93 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

9: DIBAL-H / toluene / 3.5 h / -78 °C

10: HCl / 20 h / Ambient temperature

11: n-Bu₄NF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; aluminium trichloride; dimethylsulfide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; benzene;

DOI:10.1016/0957-4166(96)00424-7

Reference yield:

2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → ((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol (185627-33-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 94 percent / TsOH / 12 h / Ambient temperature

2: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

3: methanol / 20 h

4: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

5: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

6: 93 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

7: DIBAL-H / toluene / 3.5 h / -78 °C

8: HCl / 20 h / Ambient temperature

9: n-Bu₄NF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; lithium hydroxide; N-chloro-succinimide; dimethylsulfide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/0957-4166(96)00424-7

upstream raw materials:

((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane

dimethyl 2,3-O-benzylidene-L-tartrate

2-O-benzyl-3,4-O-isopropylidene-L-threitol

2-O-benzyl-L-threitol