(Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester

Base Information

• Chemical Name: (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester
• CAS No.: 154345-03-6
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423

Synonyms:(Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester

Chemical Property of (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester

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Technology Process of (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester

There total 2 articles about (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester 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: 78.0%

tert-butyl acetoacetate (1694-31-1) + benzyl 2,3-anhydro-4-O-trifluoromethanesulfonyl-β-L-ribopyranoside (71204-45-0) → (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester (154345-03-6)

Guidance literature:

With n-butyllithium; sodium hydride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1016/S0040-4039(00)61547-2

Reference yield: 22.0%

tert-butyl acetoacetate (1694-31-1) + Methanesulfonic acid (1S,2S,5S,6R)-2-benzyloxy-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester → (E)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<4',3':2,3>furan-5-ylidenessigsaeure-tert-butylester + (Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester (154345-03-6)

Guidance literature:

With n-butyllithium; sodium hydride; In tetrahydrofuran; at 0 ℃; for 6h;

DOI:10.1016/S0040-4039(00)61547-2

Reference yield: 94.0%

(Z)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester (154345-03-6) → (E)-3',4'-Didesoxy-2,3,4,5-tetrahydro-(benzyl-α-D-arabinopyranosido)<3',4':2,3>furan-5-ylidenessigsaeure-tert-butylester

Guidance literature:

With trifluoroacetic acid; In dichloromethane; 1.) 0 deg C, 1.5 h, 2.) r.t., 3.5 h;

upstream raw materials:

tert-butyl acetoacetate

benzyl 2,3-anhydro-4-O-trifluoromethanesulfonyl-β-L-ribopyranoside

Downstream raw materials:

(3aR,6R,7S,7aR)-6-Benzyloxy-7-hydroxy-tetrahydro-furo[3,2-c]pyran-2-one

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