Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:848827-63-4
Molecular Formula:C₄₄H₆₅N₃O₁₀
Molecular Weight:796.014
Hs Code.:

Synonyms:Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 12 articles about Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 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: 60.0%

: 202812-10-0
(2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol

: 848827-56-5
p-methylphenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside

: 848827-63-4
Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -15 ℃;
DOI:10.1016/j.tet.2004.12.027

Reference yield:

: 4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1
(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

: 848827-63-4
Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine / 6 h / 80 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / 0 °C

2.2: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

3.1: 91 percent / hydrogen / palladium(II) hydroxide / ethyl acetate

4.1: 2,6-lutidine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -40 °C

5.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

6.1: 65 percent / acetic acid / methanol / 60 °C

7.1: pyridine

8.1: sodium hydride / dimethylformamide

9.1: acetic acid / H₂O

10.1: 60 percent / N-iodosuccinimide; molecular sieves 4 Angstroem; trifluoromethanesulfonic acid / CH₂Cl₂ / -15 °C

With pyridine; 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; sodium hydride; acetic acid; tetramethylguanidinum azide; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 2.2: Wittig reaction;
DOI:10.1016/j.tet.2004.12.027

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-lyxose

: 848827-63-4
Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2S,3S,4R)-2-azido-3,4-bis-benzyloxy-octadecyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: camphorsulfonic acid

2.1: pyridine / 6 h / 80 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / 0 °C

3.2: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C

4.1: 91 percent / hydrogen / palladium(II) hydroxide / ethyl acetate

5.1: 2,6-lutidine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -40 °C

6.1: 76 mg / tetramethylguanidinium azide / CH₂Cl₂ / -40 - 20 °C

7.1: 65 percent / acetic acid / methanol / 60 °C

8.1: pyridine

9.1: sodium hydride / dimethylformamide

10.1: acetic acid / H₂O

11.1: 60 percent / N-iodosuccinimide; molecular sieves 4 Angstroem; trifluoromethanesulfonic acid / CH₂Cl₂ / -15 °C

With pyridine; 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; acetic acid; tetramethylguanidinum azide; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 3.2: Wittig reaction;
DOI:10.1016/j.tet.2004.12.027