(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

Base Information

Chemical Name:(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid
CAS No.:740840-66-8
Molecular Formula:C₃₁H₃₄O₈
Molecular Weight:534.606
Hs Code.:

Synonyms:(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

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Chemical Property of (1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

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Technology Process of (1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

There total 4 articles about (1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid 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:

: 740840-64-6
3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

: 740840-66-8
(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/anie.200353478

Reference yield:

: 232603-06-4
ethyl (methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-octopyranosid)uronate

: 740840-66-8
(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / TMSOTf / acetonitrile / 8 h / 0 °C

2: 87 percent / OsO₄; aq. NaIO₄ / tetrahydrofuran / 1.5 h / 20 °C

3: 95 percent / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 6 h / 20 °C

4: 716 mg / aq. LiOH / tetrahydrofuran / 0 - 20 °C

With lithium hydroxide; sodium chlorite; sodium periodate; dipotassium hydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; acetonitrile; tert-butyl alcohol;
DOI:10.1002/anie.200353478

Reference yield:

: 740840-62-4
ethyl ((1R)-2,3,4-tri-O-benzyl-1-ethanal-1,6,7-trideoxy-α-D-gluco-octopyranosiduronate)

: 740840-66-8
(1R)-2,3,4-tri-O-benzyl-1-ethanoic acid-1,6,7-trideoxy-α-D-gluco-octopyranosiduronic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / 2-methyl-2-butene; aq. NaClO₂; K₂HPO₄ / 2-methyl-propan-2-ol / 6 h / 20 °C

2: 716 mg / aq. LiOH / tetrahydrofuran / 0 - 20 °C

With lithium hydroxide; sodium chlorite; dipotassium hydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1002/anie.200353478