tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside
CAS No.:125284-35-7
Molecular Formula:C₂₉H₄₅NO₁₀SeSi
Molecular Weight:674.723
Hs Code.:

tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside

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Chemical Property of tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside

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Technology Process of tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside

There total 13 articles about tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside 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: 92.0%

: 108-24-7
acetic anhydride

: 125284-44-8,133796-14-2
tert-butyldimethylsilyl 5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside

: 125284-35-7,133796-13-1,133796-39-1,133796-40-4,133796-41-5
tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside

Guidance literature:: With 2-(Dimethylamino)pyridine; In pyridine; dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo00003a041

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 125284-35-7,133796-13-1,133796-39-1,133796-40-4,133796-41-5
tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-threo-L-talo-α-octofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

3: 55 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 50 °C

4: 92 percent / 2-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; 2-(Dimethylamino)pyridine; lithium aluminium tetrahydride; tributylphosphine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo00003a041

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 125284-35-7,133796-13-1,133796-39-1,133796-40-4,133796-41-5
tert-butyldimethylsilyl 6-O-acetyl-5-deoxy-5-C-(((2-nitrophenyl)selenyl)methyl)-2,3:7,8-di-O-isopropylidene-D-erythro-D-talo-α-octofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 9 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

3: 1) Bu₃P, 2) DMAP / 1) THF, 50 deg C, 1 h, 2) pyridine, 20 deg C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; tributylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00003a041