3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

Base Information

Chemical Name:3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid
CAS No.:794568-38-0
Molecular Formula:C₂₆H₃₀O₉
Molecular Weight:486.519
Hs Code.:

Synonyms:3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

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Chemical Property of 3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

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Technology Process of 3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

There total 4 articles about 3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic 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:

: 794568-37-9
3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-carboxymethyl-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

: 794568-38-0
3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;
DOI:10.1021/jo040203w

Reference yield:

: 740840-47-5
3-((2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

: 794568-38-0
3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / TMSOTf / acetonitrile / 12 h / 0 °C

2: 91 percent / OsO₄; sodium metaperiodate / tetrahydrofuran; H₂O / 3 h / 20 °C

3: 95 percent / 2-methyl-2-butene; potassium phosphate monobasic; sodium chlorite / 2-methyl-propan-2-ol; H₂O / 6 h / 20 °C

4: 400 mg / LiOH / tetrahydrofuran; H₂O / 0 - 20 °C

With lithium hydroxide; sodium chlorite; sodium periodate; potassium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo040203w

Reference yield:

: 794568-36-8
3-[(2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3-methoxycarbonylmethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propionic acid ethyl ester

: 794568-38-0
3-((2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3,6-bis-carboxymethyl-tetrahydro-pyran-2-yl)-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / 2-methyl-2-butene; potassium phosphate monobasic; sodium chlorite / 2-methyl-propan-2-ol; H₂O / 6 h / 20 °C

2: 400 mg / LiOH / tetrahydrofuran; H₂O / 0 - 20 °C

With lithium hydroxide; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1021/jo040203w