2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

Base Information

Chemical Name:2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol
CAS No.:144382-53-6
Molecular Formula:C₅₆H₆₆N₂O₁₇Si
Molecular Weight:1067.23
Hs Code.:

2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

Synonyms:2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

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Chemical Property of 2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

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Technology Process of 2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

There total 7 articles about 2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol 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: 50.0%

: 87190-67-8
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

: 144382-52-5
2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-D-mannitol

: 144382-53-6
2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 1.5h;

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 144382-53-6
2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 18 h / Ambient temperature

2: THF, 1) -55 deg C, 15 min., 2) -55 deg C, 0.5 h

3: 86 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / Ambient temperature

4: 50 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: (2S,3R,4R,5R)-5-Benzyloxy-2-formyl-4-hydroxy-3-(4-methoxy-benzyloxy)-piperidine-1-carboxylic acid benzyl ester

: 144382-53-6
2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

Guidance literature:: Multi-step reaction with 5 steps

1: aq. NaBH₄ / ethanol / 1) 0 deg C, 0.5 h, 2) 0 deg C to RT, 0.5 h

2: 97 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 18 h / Ambient temperature

3: THF, 1) -55 deg C, 15 min., 2) -55 deg C, 0.5 h

4: 86 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / Ambient temperature

5: 50 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;