(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

Base Information

Chemical Name:(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid
CAS No.:1190850-94-2
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

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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 (2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

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Technology Process of (2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

There total 7 articles about (2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic 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: 80.0%

: 1190850-93-1
tert-butyl [(2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl]methylcarbamate

: 1190850-94-2
(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

Guidance literature:: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium chloride; potassium bromide; In acetonitrile; at 0 ℃; for 1h;
DOI:10.1002/ejoc.200900460

Reference yield:

: 1469300-19-3
C₁₉H₂₇NO₆

: 1190850-94-2
(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

Guidance literature:: With lithium hydroxide monohydrate; water; In tetrahydrofuran; d⁽⁴⁾-methanol; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/anie.201304239

Reference yield:

: C₁₃H₁₇N₃O₃

: 1190850-94-2
(2R,4S,5R)-4-(benzyloxy)-5-[(tert-butoxycarbonylamino)methyl]tetrahydrofuran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / acetonitrile / 0.17 h / 0 °C / Inert atmosphere

2: acetyl chloride / 4.5 h / 0 - 50 °C / Inert atmosphere

3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 760.05 Torr

4: lithium hydroxide monohydrate; water / d⁽⁴⁾-methanol; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; acetyl chloride; In tetrahydrofuran; d⁽⁴⁾-methanol; ethyl acetate; acetonitrile;
DOI:10.1002/anie.201304239