Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:852371-69-8
Molecular Formula:C₃₃H₄₃N₃O₇SSi
Molecular Weight:653.872
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl 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: 89.0%

: 129891-66-3
2-azido-2-deoxy-3,4-O-dibenzyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

: 98-59-9
p-toluenesulfonyl chloride

: 852371-69-8
Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With pyridine;
DOI:10.1016/j.bmcl.2005.02.061

Reference yield: 77.0%

: 52791-97-6
lithium phenylmethanethiolate

: 852371-69-8
Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

: 852371-70-1
((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: In tetrahydrofuran; at 0 - 25 ℃;
DOI:10.1016/j.bmcl.2005.02.061

Reference yield:

: 852371-69-8
Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

: (3aS,4R,5S,6S,7R,7aR)-4-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / tetrahydrofuran / 0 - 25 °C

2: 86 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

3: K₂CO₃

4: trimethylsilyl triflate; 4 Angstroem molecular sieves / diethyl ether / -42 °C

5: aq. LiOH / tetrahydrofuran

6: pyridine

With pyridine; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; In tetrahydrofuran; diethyl ether; 3: Schmidt's reaction;
DOI:10.1016/j.bmcl.2005.02.061