tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

Base Information

Chemical Name:tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate
CAS No.:955375-97-0
Molecular Formula:C₄₂H₄₈O₈
Molecular Weight:680.838
Hs Code.:

Synonyms:tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

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Technology Process of tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

There total 4 articles about tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate 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: 35.0%

: 120520-77-6
2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

: 35059-50-8
t-butyl diazoacetate

: 955375-97-0
tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;
DOI:10.1021/jo071221r

Reference yield:

: 955376-01-9
2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)acetic acid

: 955375-97-0
tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP; isopropenyl chloroformate / CH₂Cl₂ / -5 °C

2: 449 mg / 0.25 h / microwave irradiation

With dmap; Isopropenyl chloroformate; In dichloromethane;
DOI:10.1021/jo071221r

Reference yield:

: 120520-77-6
2-{(2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl] tetrahydro-2H-pyran-2-yl}acetaldehyde

: 955375-97-0
tert-butyl 3-oxo-4-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)butanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / aq. H₂O₂; KH₂PO₄; NaClO₂ / acetonitrile; H₂O / 2 h / 20 °C

2: DMAP; isopropenyl chloroformate / CH₂Cl₂ / -5 °C

3: 449 mg / 0.25 h / microwave irradiation

With dmap; sodium chlorite; potassium dihydrogenphosphate; Isopropenyl chloroformate; dihydrogen peroxide; In dichloromethane; water; acetonitrile;
DOI:10.1021/jo071221r