tert-butyl 2,2-dimethyl-4-{(R)-{(2S,3S,4S)-5-oxo-3,4-bis[(trimethylsilyl)oxy]tetrahydrofuran-2-yl}[(trimethylsilyl)oxy]methyl}-1,3-oxazolidine-3-carboxylate (non-preferred name)

Base Information

• Chemical Name: tert-butyl 2,2-dimethyl-4-{(R)-{(2S,3S,4S)-5-oxo-3,4-bis[(trimethylsilyl)oxy]tetrahydrofuran-2-yl}[(trimethylsilyl)oxy]methyl}-1,3-oxazolidine-3-carboxylate (non-preferred name)
• CAS No.: 135086-50-9
• Molecular Formula: C₂₄H₄₉NO₈Si₃
• Molecular Weight: 563.911
• Mol file: 135086-50-9.mol

Synonyms:

Chemical Property of tert-butyl 2,2-dimethyl-4-{(R)-{(2S,3S,4S)-5-oxo-3,4-bis[(trimethylsilyl)oxy]tetrahydrofuran-2-yl}[(trimethylsilyl)oxy]methyl}-1,3-oxazolidine-3-carboxylate (non-preferred name)

Chemical Property:

• Vapor Pressure: 6.34E-12mmHg at 25°C
• Boiling Point: 544.7°Cat760mmHg
• Flash Point: 283.2°C
• Density: 1.06g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 2,2-dimethyl-4-{(R)-{(2S,3S,4S)-5-oxo-3,4-bis[(trimethylsilyl)oxy]tetrahydrofuran-2-yl}[(trimethylsilyl)oxy]methyl}-1,3-oxazolidine-3-carboxylate (non-preferred name)

There total 5 articles about tert-butyl 2,2-dimethyl-4-{(R)-{(2S,3S,4S)-5-oxo-3,4-bis[(trimethylsilyl)oxy]tetrahydrofuran-2-yl}[(trimethylsilyl)oxy]methyl}-1,3-oxazolidine-3-carboxylate (non-preferred name) 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:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (R)-2,2-Dimethyl-4-[(R)-((2R,3R,4R)-5-oxo-3,4-bis-trimethylsilanyloxy-tetrahydro-furan-2-yl)-trimethylsilanyloxy-methyl]-oxazolidine-3-carboxylic acid tert-butyl ester (135086-50-9,136597-85-8,136597-86-9,136597-87-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 8 h / -80 °C

2: 65 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: dicyclohexane-crown-6, KMnO₄ / CH₂Cl₂ / 1) 15 deg C, 3 h, 2) room temp., 3 h

5: pyridine / 5 h / Ambient temperature

With pyridine; dmap; potassium permanganate; dicyclohexane-crown-6; boron trifluoride diethyl etherate; triethylamine; In dichloromethane;

DOI:10.1021/jo00023a015

Reference yield:

6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-ribo-hept-2-enono-1,4-lactone (127997-06-2) → (R)-2,2-Dimethyl-4-[(R)-((2R,3R,4R)-5-oxo-3,4-bis-trimethylsilanyloxy-tetrahydro-furan-2-yl)-trimethylsilanyloxy-methyl]-oxazolidine-3-carboxylic acid tert-butyl ester (135086-50-9,136597-85-8,136597-86-9,136597-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 3 h / Ambient temperature

2: dicyclohexane-crown-6, KMnO₄ / CH₂Cl₂ / 1) 15 deg C, 3 h, 2) room temp., 3 h

3: pyridine / 5 h / Ambient temperature

With pyridine; potassium permanganate; dicyclohexane-crown-6; In dichloromethane;

DOI:10.1021/jo00023a015

Reference yield:

6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-arabino-hept-2-enono-1,4-lactone (127997-05-1) → (R)-2,2-Dimethyl-4-[(R)-((2R,3R,4R)-5-oxo-3,4-bis-trimethylsilanyloxy-tetrahydro-furan-2-yl)-trimethylsilanyloxy-methyl]-oxazolidine-3-carboxylic acid tert-butyl ester (135086-50-9,136597-85-8,136597-86-9,136597-87-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / Ambient temperature

2: pyridine / 3 h / Ambient temperature

3: dicyclohexane-crown-6, KMnO₄ / CH₂Cl₂ / 1) 15 deg C, 3 h, 2) room temp., 3 h

4: pyridine / 5 h / Ambient temperature

With pyridine; dmap; potassium permanganate; dicyclohexane-crown-6; triethylamine; In dichloromethane;

DOI:10.1021/jo00023a015

upstream raw materials:

chloro-trimethyl-silane

(R)-4-[(R)-((2S,3S,4R)-3,4-Dihydroxy-5-oxo-tetrahydro-furan-2-yl)-trimethylsilanyloxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

6,7-N,O-Isopropylidene-6-<(tert-butoxycarbonyl)amino>-2,3,6-trideoxy-D-ribo-hept-2-enono-1,4-lactone

Downstream raw materials:

(S)-tert-Butoxycarbonylamino-((2R,3R,4R,5R,6S)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester

(R)-2,2-Dimethyl-4-((2R,3S,4S,5S,6R)-3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-yl)-oxazolidine-3-carboxylic acid tert-butyl ester

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