ethyl dl-threo-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate

Base Information

• Chemical Name: ethyl dl-threo-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate
• CAS No.: 115690-00-1
• Molecular Formula: C₂₁H₃₀O₇
• Molecular Weight: 394.465
• Mol file: 115690-00-1.mol

Synonyms:

Chemical Property of ethyl dl-threo-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl dl-threo-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate

There total 18 articles about ethyl dl-threo-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate 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: 73.0%

dl-erythro-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol (115689-96-8,115689-98-0,127000-45-7,127000-46-8) + diethyl malonate (105-53-3) → ethyl dl-erythro-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate (115690-00-1,115690-01-2,126906-82-9,126906-98-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 95 ℃; for 3h;

DOI:10.1248/cpb.37.2379

Reference yield:

benzaldehyde (100-52-7) → ethyl dl-erythro-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate (115690-00-1,115690-01-2,126906-82-9,126906-98-7)

Guidance literature:

Multi-step reaction with 6 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

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1248/cpb.37.2379

Reference yield:

dl-2-O-benzylerythritol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → ethyl dl-erythro-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate (115690-00-1,115690-01-2,126906-82-9,126906-98-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / p-TsOH (H₂O) / benzene / 3 h / Heating

2: 13.11 g / Et₃N / benzene / 1 h / Ambient temperature

3: 95 percent / NaI, NaHCO₃ / acetone / 14 h / Heating

4: 73 percent / 55percent NaH / dimethylformamide / 3 h / 95 °C

With sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.37.2379

upstream raw materials:

<4S,4(1S)>-4-(1-Benzyloxy-2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

diethyl malonate

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

Methanesulfonic acid (S)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Downstream raw materials:

(2R,3S)-2-(3,5-dinitrobenzoyloxy)methyltetrahydropyran-3-yl 3,5-dinitrobenzoate

(2S,3S)-3-benzyloxy-6-(tert-butyldiphenylsiloxy)-1-triphenylmethoxyhexan-2-ol

Methanesulfonic acid (1S,2S)-2-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-1-trityloxymethyl-pentyl ester

(2R,3S)-<3-(benzyloxy)tetrahydropyran-2-yl>methanol