2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam

Base Information

• Chemical Name: 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam
• CAS No.: 294204-04-9
• Molecular Formula: C₂₉H₃₃NO₇
• Molecular Weight: 507.584
• Mol file: 294204-04-9.mol

Synonyms:2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam

Chemical Property of 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam

There total 9 articles about 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam 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: 67.0%

5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone (294204-02-7) → 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam (294204-04-9)

Guidance literature:

5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone; With triphenylphosphine; In acetonitrile; at 20 ℃;

at 20 ℃; Further stages.;

DOI:10.1021/jo000141j

Reference yield:

5,6-O-isopropylidene-D-galactonic acid γ-lactone (56710-46-4,67321-94-2,69602-93-3,94697-68-4,100227-29-0,102355-63-5,121357-95-7) → 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam (294204-04-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 68 percent / iPr₂NEt; n-Bu₄NI / dimethylformamide / 50 °C

2.1: 93 percent / aq. AcOH / 20 °C

3.1: (n-Bu)2SnO; MS 4A / benzene / Heating

3.2: 47 percent / iPr₂NEt / dimethylformamide / 3 h / 20 °C

4.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: 34 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / -50 °C

6.1: pyridine / CH₂Cl₂ / 2 h / -40 °C

7.1: NaN₃ / dimethylformamide / 20 °C

8.1: PPh₃ / acetonitrile / 20 °C

8.2: 67 percent / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: stannylation / 3.2: Substitution / 4.1: Oxidation / 5.1: Reduction / 6.1: Substitution / 7.1: Substitution / 8.1: Addition / 8.2: Hydrolysis;

DOI:10.1021/jo000141j

Reference yield:

trityl chloride (76-83-5) → 2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-glucono-δ-lactam (294204-04-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (n-Bu)2SnO; MS 4A / benzene / Heating

1.2: 47 percent / iPr₂NEt / dimethylformamide / 3 h / 20 °C

2.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 34 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / -50 °C

4.1: pyridine / CH₂Cl₂ / 2 h / -40 °C

5.1: NaN₃ / dimethylformamide / 20 °C

6.1: PPh₃ / acetonitrile / 20 °C

6.2: 67 percent / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; di(n-butyl)tin oxide; Dess-Martin periodane; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: stannylation / 1.2: Substitution / 2.1: Oxidation / 3.1: Reduction / 4.1: Substitution / 5.1: Substitution / 6.1: Addition / 6.2: Hydrolysis;

DOI:10.1021/jo000141j

upstream raw materials:

5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

5,6-O-isopropylidene-D-galactonic acid γ-lactone

trityl chloride

2,3-di-O-methoxymethyl-D-galactono-γ-lactone

Downstream raw materials:

nojirimycin-δ-lactam