3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

Base Information

Chemical Name:3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone
CAS No.:639820-25-0
Molecular Formula:C₃₂H₃₇NO₆Si
Molecular Weight:559.734
Hs Code.:

Synonyms:3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

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Chemical Property of 3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

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Technology Process of 3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

There total 7 articles about 3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-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: 53.0%

: 107-18-6
allyl alcohol

: 639820-24-9
(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

: 639820-25-0
3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

Guidance literature:: With boron trifluoride diethyl etherate; In chloroform; at 50 ℃; for 20h;
DOI:10.1021/jo035039b

Reference yield:

: 92512-33-9
(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

: 639820-25-0
3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / pyridine / CH₂Cl₂ / 3.25 h / -78 - -25 °C

2: 64 percent / dimethylformamide / 0.5 h / -60 °C

3: DDQ / CH₂Cl₂; H₂O / 24 h / 20 °C

4: 1.29 g / pyridine; DMAP / CH₂Cl₂; H₂O / 2 h / 20 °C

5: 53 percent / boron trifluoride etherate / CHCl₃ / 20 h / 50 °C

With pyridine; dmap; boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035039b

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 639820-25-0
3-O-allyl-2-N-(benzyloxycarbonyl)amino-5-O-(tert-butyldiphenylsilyl)-2-deoxy-D-xylono-1,4-lactone

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / imidazole / dimethylformamide / 1 h / 0 - 20 °C

2: 78 percent / pyridine / CH₂Cl₂ / 3.25 h / -78 - -25 °C

3: 64 percent / dimethylformamide / 0.5 h / -60 °C

4: DDQ / CH₂Cl₂; H₂O / 24 h / 20 °C

5: 1.29 g / pyridine; DMAP / CH₂Cl₂; H₂O / 2 h / 20 °C

6: 53 percent / boron trifluoride etherate / CHCl₃ / 20 h / 50 °C

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035039b