(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

Base Information

Chemical Name:(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate
CAS No.:691371-46-7
Molecular Formula:C₆₀H₅₃N₃O₆
Molecular Weight:912.097
Hs Code.:

Synonyms:(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

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Chemical Property of (1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

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Technology Process of (1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

There total 6 articles about (1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate 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: 68.0%

: 691371-42-3
(3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate

: 691371-46-7
(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

Guidance literature:: (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate; With lithium azide; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;

With sulfuric acid; In tetrahydrofuran; at 20 ℃;
DOI:10.1135/cccc20040435

Reference yield:

: 76-83-5
trityl chloride

: 691371-46-7
(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / pyridine / 1 h / 100 °C

2.1: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

3.1: pyridine / 20 °C

4.1: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

5.1: LiN₃ / dimethylformamide / 1.5 h / 60 °C

5.2: 68 percent / aq. H₂SO₄ / tetrahydrofuran / 20 °C

With pyridine; ruthenium trichloride; thionyl chloride; lithium azide; potassium metaperiodate; triethylamine; In tetrachloromethane; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1135/cccc20040435

Reference yield:

: 360562-15-8
(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

: 691371-46-7
(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / pyridine / 1 h / 100 °C

2.1: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

3.1: pyridine / 20 °C

4.1: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

5.1: LiN₃ / dimethylformamide / 1.5 h / 60 °C

5.2: 68 percent / aq. H₂SO₄ / tetrahydrofuran / 20 °C

With pyridine; ruthenium trichloride; thionyl chloride; lithium azide; potassium metaperiodate; triethylamine; In tetrachloromethane; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1135/cccc20040435