allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

Base Information

Chemical Name:allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide
CAS No.:156325-67-6
Molecular Formula:C₂₃H₃₆N₂O₇Si
Molecular Weight:480.634
Hs Code.:

Synonyms:allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

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Chemical Property of allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

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Technology Process of allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

There total 10 articles about allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide 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:

: (2,2,2-Trichloro-acetyl)-carbamic acid (2R,3R,4S,5S,6S)-2-allyloxy-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-carbamoyl-tetrahydro-pyran-4-yl ester

: 156325-67-6
allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

Guidance literature:: With zinc; In methanol; at 20 ℃; for 5h; Yield given;
DOI:10.1016/S0040-4020(01)85066-3

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 156325-67-6
allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / imidazol / dimethylformamide / 120 h / 40 °C

2: 50 percent / lithium aluminium hydride, aluminium trichloride / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

4: 2-methyl-2-butene, sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C

5: 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

6: ammonia / CH₂Cl₂ / 0.67 h / 0 °C

7: 70 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

8: CH₂Cl₂ / 14 h / 20 °C

9: Zn dust / methanol / 5 h / 20 °C

With 1H-imidazole; sodium chlorite; lithium aluminium tetrahydride; aluminium trichloride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; dimethyl sulfoxide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)85066-3

Reference yield:

: 20746-64-9,65987-12-4,71925-95-6,81600-93-3,84276-56-2,93382-48-0,100759-10-2,103619-31-4,119237-85-3,119237-96-6,146985-88-8
allyl (R)-4,6-O-benzylidene-β-D-gluco-pyranoside

: 156325-67-6
allyl 4-O-benzyl-2-O-t-butyldimethylsilyl-3-O-carbamoyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / imidazol / dimethylformamide / 120 h / 40 °C

2: 50 percent / lithium aluminium hydride, aluminium trichloride / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

4: 2-methyl-2-butene, sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C

5: 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

6: ammonia / CH₂Cl₂ / 0.67 h / 0 °C

7: 70 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

8: CH₂Cl₂ / 14 h / 20 °C

9: Zn dust / methanol / 5 h / 20 °C

With 1H-imidazole; sodium chlorite; lithium aluminium tetrahydride; aluminium trichloride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; dimethyl sulfoxide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)85066-3