(2R,3S)-7-Benzyloxy-heptane-1,2,3-triol

Base Information

• Chemical Name: (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol
• CAS No.: 102354-75-6
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.326
• Mol file: 102354-75-6.mol

Synonyms:

Chemical Property of (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol

There total 6 articles about (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol 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:

1 ,5-pentanediol (111-29-5) → (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol (102354-75-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / tetrahydrofuran; dimethylformamide / -25 °C

2: PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 25 °C

3: CH₂Cl₂ / 25 °C

4: Diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 °C

5: 1.) t-BuOOH, (i-PrO)4Ti, L-(+)-diethyl tartarate 2,) 0.5N NaOH / 1.) CH₂Cl₂, -20 deg C 2.) H₂O, t-BuOH, 70 deg C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80851-0

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol (102354-75-6)

Guidance literature:

Multi-step reaction with 4 steps

1: PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 25 °C

2: CH₂Cl₂ / 25 °C

3: Diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 °C

4: 1.) t-BuOOH, (i-PrO)4Ti, L-(+)-diethyl tartarate 2,) 0.5N NaOH / 1.) CH₂Cl₂, -20 deg C 2.) H₂O, t-BuOH, 70 deg C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; pyridinium chlorochromate; In hexane; dichloromethane;

DOI:10.1016/S0040-4039(01)80851-0

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → (2R,3S)-7-Benzyloxy-heptane-1,2,3-triol (102354-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 25 °C

2: Diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 °C

3: 1.) t-BuOOH, (i-PrO)4Ti, L-(+)-diethyl tartarate 2,) 0.5N NaOH / 1.) CH₂Cl₂, -20 deg C 2.) H₂O, t-BuOH, 70 deg C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; In hexane; dichloromethane;

DOI:10.1016/S0040-4039(01)80851-0

upstream raw materials:

(E)-7-(benzyloxy)-2-hepten-1-ol

1 ,5-pentanediol

5-(benzyloxy)-1-pentanol

5-benzyloxy-1-pentanal

Downstream raw materials:

(2R,3S)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3-diol

[(4R,5S)-5-(4-Benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane