(2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 114976-68-0
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 114976-68-0.mol

Synonyms:(2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Chemical Property of (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

There total 9 articles about (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde 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:

[(2S,4S,6S)-4-(benzyloxy)-6-methoxytetrahydro-pyran-2-yl]-methanol (87391-88-6) → (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde (114976-68-0)

Guidance literature:

With pyridinium trifluroacetate; oxalic acid; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) DMSO, benzene, 25 deg C, 18 h, 2.) diethyl ether, methanol, 30 min;

DOI:10.1021/jo00248a010

Reference yield:

benzyl bromide (100-39-0) → (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde (114976-68-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂SnO / benzene / 16 h / Heating

1.2: 49 percent / n-Bu₄NI / benzene / 4 h / Heating

2.1: 87 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: NaH; imidazole / tetrahydrofuran / 7 h / 20 °C

3.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

4.1: AIBN; n-Bu₃SnH / toluene / 36 h / Heating

5.1: 2.05 g / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

6.1: oxalyl chloride; DMSO; iPr₂NEt / CH₂Cl₂ / 2 h / -70 - 20 °C

With 1H-imidazole; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6.1: Swern oxidation;

DOI:10.1016/S0040-4020(03)01103-7

Reference yield:

methyl α-D-galactopyranoside 3-benzyl ether (40010-11-5,61277-64-3,65942-01-0,81371-53-1,93714-01-3,108644-64-0,133268-63-0,133268-64-1,143005-10-1,143005-11-2,81371-52-0) → (2S,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde (114976-68-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 87 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: NaH; imidazole / tetrahydrofuran / 7 h / 20 °C

2.2: 90 percent / tetrahydrofuran / 12 h / 20 °C

3.1: AIBN; n-Bu₃SnH / toluene / 36 h / Heating

4.1: 2.05 g / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

5.1: oxalyl chloride; DMSO; iPr₂NEt / CH₂Cl₂ / 2 h / -70 - 20 °C

With 1H-imidazole; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;

DOI:10.1016/S0040-4020(03)01103-7

upstream raw materials:

[(2S,4S,6S)-4-(benzyloxy)-6-methoxytetrahydro-pyran-2-yl]-methanol

benzyl bromide

methyl α-D-galactopyranoside 3-benzyl ether

(2S,4S,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran

Downstream raw materials:

methyl 3-O-benzyl-2,4,6-trideoxy-α-D-threo-hept-6-ynopyranoside

4-<2-<(2RS,4S)-4-benzyloxy-6-methoxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>-1-ene-ethyl>-3-pyridine carboxamide