(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

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Chemical Name:(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid
CAS No.:193154-29-9
Molecular Formula:C₃₇H₃₅NO₉
Molecular Weight:637.686
Hs Code.:

Synonyms:(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

There total 6 articles about (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-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: 84.0%

: 193154-26-6
N-(fluoren-9-ylmethoxycarbonyl)-2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosylamine

: 193154-29-9
(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium chloride; potassium bromide; In dichloromethane; for 0.25h;
DOI:10.1002/chem.19970030614

Reference yield:

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 193154-29-9
(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / aq. NaHCO₃, Na₂CO₃ / dioxane / 3 h

2: 96 percent / p-TsOH / methanol; CH₂Cl₂ / 2 h

3: 84 percent / aq. NaOCl, TEMPO, NaHCO₃, NaCl, KBr, Bu₄NCl / CH₂Cl₂ / 0.25 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; sodium chloride; potassium bromide; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1002/chem.19970030614

Reference yield:

: 169824-26-4
1,2-anhydro-3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside

: 193154-29-9
(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / ZnCl₂ / tetrahydrofuran / 2 h

2: aq. H₂SO₄ / tetrahydrofuran / 0.5 h

3: 87 percent / aq. NaHCO₃, Na₂CO₃ / dioxane / 3 h

4: 96 percent / p-TsOH / methanol; CH₂Cl₂ / 2 h

5: 84 percent / aq. NaOCl, TEMPO, NaHCO₃, NaCl, KBr, Bu₄NCl / CH₂Cl₂ / 0.25 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sulfuric acid; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; sodium chloride; potassium bromide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1002/chem.19970030614