(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

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Chemical Name:(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid
CAS No.:321380-67-0
Molecular Formula:C₃₆H₄₃NO₁₂
Molecular Weight:681.737
Hs Code.:

(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Synonyms:(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

There total 22 articles about (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-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: 90.0%

: 321380-51-2
methyl (2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

: 321380-67-0
(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: methyl (2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate; With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; In methanol; at 20 ℃; for 5h;
DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

: 181228-42-2
methyl 3-O-benzyl-α-L-idopyranoside

: 321380-67-0
(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 87 percent / 10-D,L-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

2.1: 2.25 g / pyridine / 0.5 h / 20 °C

3.1: acetic acid; H₂O / 0.25 h / 80 °C

4.1: 2.55 g / imidazole / dimethylformamide / 18 h / 50 °C

5.1: 1.91 g / CrO₃ / aq. H₂SO₄ / 0 °C

6.1: 1.55 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

7.1: 60 percent / Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

8.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

8.2: 60 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.17 h / -15 °C

9.1: 76 percent / Bu₃SnH; AIBN / benzene / 20 - 80 °C

10.1: H₂O₂; LiOH / tetrahydrofuran / 0 - 20 °C

10.2: 90 percent / NaOH / methanol / 5 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium hydroxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; benzene; 5.1: Jones oxidation;
DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

: 181024-52-2
methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-L-idopyranoside

: 321380-67-0
(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: 100 percent / NaOMe / methanol / 4 h / 20 °C

2.1: 87 percent / 10-D,L-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

3.1: 2.25 g / pyridine / 0.5 h / 20 °C

4.1: acetic acid; H₂O / 0.25 h / 80 °C

5.1: 2.55 g / imidazole / dimethylformamide / 18 h / 50 °C

6.1: 1.91 g / CrO₃ / aq. H₂SO₄ / 0 °C

7.1: 1.55 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

8.1: 60 percent / Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

9.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9.2: 60 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.17 h / -15 °C

10.1: 76 percent / Bu₃SnH; AIBN / benzene / 20 - 80 °C

11.1: H₂O₂; LiOH / tetrahydrofuran / 0 - 20 °C

11.2: 90 percent / NaOH / methanol / 5 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; dmap; lithium hydroxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; benzene; 6.1: Jones oxidation;
DOI:10.1016/S0008-6215(00)00234-2