ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate

Base Information

• Chemical Name: ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate
• CAS No.: 126906-91-0
• Molecular Formula: C₂₆H₄₄O₆Si
• Molecular Weight: 480.717
• Mol file: 126906-91-0.mol

Synonyms:ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate

Chemical Property of ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate

There total 18 articles about ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate 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: 90.0%

3,4-dihydro-2H-pyran (110-87-2) + ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-hydroxyhexanoate (126906-90-9,126907-04-8) → ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate (126906-91-0)

Guidance literature:

pyridinium p-toluenesulfonate; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1248/cpb.37.2379

Reference yield:

benzaldehyde (100-52-7) → ethyl dl-erythro-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate (126906-91-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 58 percent / p-TsOH (H₂O) / toluene / 8 h / Heating

2: 65 percent / LiAlH₄-AlCl₃ / diethyl ether; CH₂Cl₂ / 3 h / Ambient temperature

3: 80 percent / p-TsOH (H₂O) / benzene / 3 h / Heating

4: 13.11 g / Et₃N / benzene / 1 h / Ambient temperature

5: 95 percent / NaI, NaHCO₃ / acetone / 14 h / Heating

6: 73 percent / 55percent NaH / dimethylformamide / 3 h / 95 °C

7: 91 percent / NaCl / dimethylsulfoxide; H₂O / 2 h / 210 °C

8: 93 percent / aq. acetic acid / 1.) room temp., 1 h, 2.) 50 deg C, 2 h

9: 83 percent / Et₃N / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 6 h / Ambient temperature

10: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; sodium chloride; dmap; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1248/cpb.37.2379

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → ethyl dl-threo-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-(tetrahydropyran-2-yloxy)hexanoate (126906-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

2: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

With triethylamine; dmap; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1248/cpb.37.2379

upstream raw materials:

3,4-dihydro-2H-pyran

ethyl dl-threo-4-benzyloxy-6-(tert-butyldimethylsiloxy)-5-hydroxyhexanoate

tert-butyldimethylsilyl chloride

dl-2-O-benzyl-3,4-O-isopropylidenethreitol

Downstream raw materials:

dl-trans-4-benzyloxy-6-hexadecyloxy-5-hexanolide

dl-erythro-4-benzyloxy-6-hexadecyloxy-5-hydroxyhexanoic acid

ethyl dl-erythro-4-benzyloxy-6-hydroxy-5-(tetrahydropyran-2-yloxy)hexanoate

dl-cis-4-benzyloxy-6-hexadecyloxy-5-hexanolide