6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose

Base Information

• Chemical Name: 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose
• CAS No.: 129034-04-4
• Molecular Formula: C₂₃H₃₇NO₄SSi
• Molecular Weight: 451.703
• Mol file: 129034-04-4.mol

Synonyms:6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose

Chemical Property of 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose

There total 8 articles about 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose 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: 82.0%

5-O-tert-butyldimethylsilyl-1-deoxy-3,4-O-isopropylidene-1-phenylthio-D-erythro-pentulose (129034-03-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose (129034-04-4)

Guidance literature:

at 70 ℃; for 3h;

Reference yield:

5-deoxy-2,3-O-isopropylidene-5-phenylthio-D-lyxitol (129034-01-1) → 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose (129034-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

2: 98 percent / DMSO, dicyclohexyl carbodiimide, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C then RT, 3 h

3: 82 percent / 3 h / 70 °C

With pyridine; 1H-imidazole; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In diethyl ether; N,N-dimethyl-formamide;

Reference yield:

5-deoxy-2,3-O-isopropylidene-5-phenylthio-α-D-lyxofuranose (129034-00-0) → 6-O-tert-butyldimethylsilyl-1,2-dideoxy-1-dimethylamino-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose (129034-04-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / NaBH₄ / methanol / 3 h

2: 92 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

3: 98 percent / DMSO, dicyclohexyl carbodiimide, pyridine, trifluoroacetic acid / diethyl ether / 0 deg C then RT, 3 h

4: 82 percent / 3 h / 70 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; N,N-dimethyl-formamide;

upstream raw materials:

5-O-tert-butyldimethylsilyl-1-deoxy-3,4-O-isopropylidene-1-phenylthio-D-erythro-pentulose

N,N-dimethyl-formamide dimethyl acetal

5-deoxy-2,3-O-isopropylidene-5-phenylthio-D-lyxitol

5-deoxy-2,3-O-isopropylidene-5-phenylthio-α-D-lyxofuranose

Downstream raw materials:

6-O-tert-butyldimethylsilyl-2-deoxy-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose

Methyl-5-acetylamino-3,5-didesoxy-D-glycero-β-D-galakto-nonulopyranosidonsaeure-methylester

methyl (methyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-D-glycero-D-galacto-2-nonulopyranosid)onate

1-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-4,5-O-isopropylidene-2-phenylthio-D-erythro-hex-1-eno-3-ulose