(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol
CAS No.:852371-73-4
Molecular Formula:C₅₄H₅₇N₃O₉S
Molecular Weight:924.127
Hs Code.:

(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

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Chemical Property of (1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

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Technology Process of (1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

There total 6 articles about (1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol 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:

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

: 852371-73-4
(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / pyridine

2: 77 percent / tetrahydrofuran / 0 - 25 °C

3: 86 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

4: K₂CO₃

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

6: aq. LiOH / tetrahydrofuran

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

Reference yield:

: (3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-ol

: 852371-73-4
(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1: K₂CO₃

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

3: aq. LiOH / tetrahydrofuran

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium carbonate; In tetrahydrofuran; diethyl ether; 1: Schmidt's reaction;
DOI:10.1016/j.bmcl.2005.02.061

Reference yield:

: 2,2,2-Trichloro-acetimidic acid (3R,4R,5S,6S)-3-azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yl ester

: 852371-73-4
(1S,2R,3S,4S,5R,6S)-3-((2S,3R,4R,5S,6S)-3-Azido-4,5-bis-benzyloxy-6-benzylsulfanylmethyl-tetrahydro-pyran-2-yloxy)-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

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

2: aq. LiOH / tetrahydrofuran

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In tetrahydrofuran; diethyl ether;
DOI:10.1016/j.bmcl.2005.02.061