tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Base Information

Chemical Name:tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate
CAS No.:262286-57-7
Molecular Formula:C₃₇H₄₅NO₇
Molecular Weight:615.767
Hs Code.:

Synonyms:tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

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Chemical Property of tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

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Technology Process of tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

There total 4 articles about tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate 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: 2.0%

: 86302-43-4,35000-38-5
(tert-Butoxycarbonylmethylene)triphenylphosphorane

: 262286-49-7
2-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)ethanal

: (E)-4-((2S,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enoic acid tert-butyl ester

: 262286-57-7
tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: In tetrahydrofuran; Thermolysis;
DOI:10.1021/jo991206p

Reference yield:

: 180778-36-3
3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

: 262286-57-7
tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / NaOMe / methanol / 3 h / 20 °C

2: 94 percent / NaH / dimethylformamide / 0 - 20 °C

3: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

4: 69 percent / tetrahydrofuran / Thermolysis

With sodium periodate; osmium(VIII) oxide; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Hydrolysis / 2: Alkylation / 3: Oxidation / 4: Addition;
DOI:10.1021/jo991206p

Reference yield:

: 214193-76-7
1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene

: 262286-57-7
tert-butyl 4-(2'-(N-acetylamino)-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)but-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NaH / dimethylformamide / 0 - 20 °C

2: 99 percent / OsO₄; NaIO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.25 h

3: 69 percent / tetrahydrofuran / Thermolysis

With sodium periodate; osmium(VIII) oxide; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Alkylation / 2: Oxidation / 3: Addition;
DOI:10.1021/jo991206p