5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone

Base Information

• Chemical Name: 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone
• CAS No.: 118464-49-6
• Molecular Formula: C15H27N3O6Si
• Molecular Weight: 357.482
• DSSTox Substance ID: DTXSID70555951
• Wikidata: Q82437408
• Mol file: 118464-49-6.mol

Synonyms:118464-49-6;5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone;(3aS,6R,6aS)-6-[(1S)-1-azido-2-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one;DTXSID70555951;5-Azido-5-deoxy-6-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-D-mannonic Acid gamma-lactone;J-003758

Chemical Property of 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone

Chemical Property:

• PSA: 103.74000
• LogP: 2.58536
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 357.17199750
• Heavy Atom Count: 24
• Complexity: 554

Purity/Quality:

99% ^*data from raw suppliers

5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylideneL-Gulono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(=O)OC2C(CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O1)C(=O)O[C@@H]2[C@H](CO[Si](C)(C)C(C)(C)C)N=[N+]=[N-])C

Technology Process of 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone

There total 6 articles about 5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone 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: 61.0%

6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone (118464-47-4) → (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one (118464-49-6)

Guidance literature:

With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; for 20h;

DOI:10.1021/jo0516382

Reference yield:

Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester (118464-48-5) → (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one (118464-49-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; Yield given;

DOI:10.1016/0040-4039(88)85234-1

Reference yield:

2,3:5,6-di-O-isopropylidene-L-gulonolactone (7306-64-1) → (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one (118464-49-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / acetic acid / H₂O / 16 h / 30 °C

2: 71 percent / imidazole / dimethylformamide / 2 h / -40 °C

3: pyridine; CH₂Cl₂ / 1 h / -30 °C

4: NaN₃ / dimethylformamide / 3 h

With 1H-imidazole; sodium azide; acetic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(89)80059-6

upstream raw materials:

Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester

6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone

2,3:5,6-di-O-isopropylidene-L-gulonolactone

2,3-O-isopropylidene-L-gulono-γ-lactone

Downstream raw materials:

(3aR,4S,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

β-1-C-phenyl-deoxymannojirimycin

1-deoxymannojirimycin

D-Mannonolactam

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