(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Base Information

Chemical Name:(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
CAS No.:714957-37-6
Molecular Formula:C₅₄H₅₇N₃O₉
Molecular Weight:892.061
Hs Code.:

Synonyms:(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

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Chemical Property of (1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

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Technology Process of (1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

There total 10 articles about (1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol 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: 94.0%

: 714957-36-5
1D-6-O-(2-azido-3,4-di-O-benzyl-2,6-dideoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol

: 714957-37-6
(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.carres.2004.02.026

Reference yield:

: 324739-92-6
2-azido-3,4-di-O-benzyl-2,6-dideoxy-D-glucopyranosyl fluoride

: 714957-37-6
(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / 1,1,3,3-tetramethylurea; AgClO₄ / Cp₂ZrCl₂ / toluene; dioxane / 22 h

2: 94 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With silver perchlorate; trifluoroacetic acid; tetramethylurea; zirconocene dichloride; In 1,4-dioxane; dichloromethane; toluene;
DOI:10.1016/j.carres.2004.02.026

Reference yield:

: 100-39-0
benzyl bromide

: 714957-37-6
(1R,2S,3S,4R,5S,6S)-2-((2R,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.2 g / NaH / dimethylformamide / 0.5 h / 20 °C

2: 42 percent / HCl / acetic acid; H₂O / 48 h / 90 - 100 °C

3: 81 percent / DAST / 1,2-dichloro-ethane / 20 °C

4: 50 percent / 1,1,3,3-tetramethylurea; AgClO₄ / Cp₂ZrCl₂ / toluene; dioxane / 22 h

5: 94 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; silver perchlorate; sodium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; tetramethylurea; zirconocene dichloride; In 1,4-dioxane; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.carres.2004.02.026