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

Base Information

Chemical Name:3-O-(2-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-5-O-benzyl-N-benzyloxycarbonyl-1-O-(tert-butyldimethylsilyl)-4-O-carboxymethyl-D-mannitol
CAS No.:144382-54-7
Molecular Formula:C₄₃H₆₀N₂O₁₆Si
Molecular Weight:889.039
Hs Code.:

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

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

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

There total 10 articles about 3-O-(2-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-5-O-benzyl-N-benzyloxycarbonyl-1-O-(tert-butyldimethylsilyl)-4-O-carboxymethyl-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:

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

: 144382-54-7
3-O-(2-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-5-O-benzyl-N-benzyloxycarbonyl-1-O-(tert-butyldimethylsilyl)-4-O-carboxymethyl-D-mannitol

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

2: 97 percent / aq. KOH / dioxane; methanol / 1 h / Ambient temperature

3: 1) NH₂-NH₂*H₂O, 2) pyridine / 1) EtOH, reflux, 21 h, 2) RT, 18 h

With pyridine; potassium hydroxide; boron trifluoride diethyl etherate; hydrazine hydrate; In 1,4-dioxane; methanol; dichloromethane;

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 144382-54-7
3-O-(2-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-5-O-benzyl-N-benzyloxycarbonyl-1-O-(tert-butyldimethylsilyl)-4-O-carboxymethyl-D-mannitol

Guidance literature:: Multi-step reaction with 6 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

5: 97 percent / aq. KOH / dioxane; methanol / 1 h / Ambient temperature

6: 1) NH₂-NH₂*H₂O, 2) pyridine / 1) EtOH, reflux, 21 h, 2) RT, 18 h

With pyridine; 1H-imidazole; dmap; potassium hydroxide; boron trifluoride diethyl etherate; hydrazine hydrate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; 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

: 144382-54-7
3-O-(2-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-5-O-benzyl-N-benzyloxycarbonyl-1-O-(tert-butyldimethylsilyl)-4-O-carboxymethyl-D-mannitol

Guidance literature:: Multi-step reaction with 7 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

6: 97 percent / aq. KOH / dioxane; methanol / 1 h / Ambient temperature

7: 1) NH₂-NH₂*H₂O, 2) pyridine / 1) EtOH, reflux, 21 h, 2) RT, 18 h

With pyridine; 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrazine hydrate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;