(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

Base Information

Chemical Name:(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate
CAS No.:914982-61-9
Molecular Formula:C₂₉H₃₅NO₈S
Molecular Weight:557.665
Hs Code.:

Synonyms:(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

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Chemical Property of (2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

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Technology Process of (2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

There total 10 articles about (2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate 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: 80.0%

: 914982-60-8
(R)-2-benzyloxy-1-((4S,5R)-5-((S)-2-(benzyloxy)-1-(tosylamino)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate

: 914982-61-9
(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

Guidance literature:: With iron(III) chloride; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2006.08.035

Reference yield:

: 914982-58-4
(R)-1-((4S,5R)-5-((S)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(benzyloxy)ethyl acetate

: 914982-61-9
(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / hydrogen / Lindlar's catalyst / methanol / 4 h / 20 °C / 760 Torr

2: 86 percent / pyridine / 3 h / 0 - 20 °C

3: 80 percent / FeCl₃*6H₂O / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; hydrogen; iron(III) chloride; Lindlar's catalyst; In methanol; dichloromethane;
DOI:10.1016/j.tet.2006.08.035

Reference yield:

: 914982-54-0
(2R,4S,5R)-4-((2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)-2-phenyl-1,3-dioxan-5-yl-4-methylbenzenesulfonamide

: 914982-61-9
(2R,3S,4R,5S)-1,6-bis(benzyloxy)-3,4-dihydroxy-5-(tosylamino)hexan-2-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 2 h / 0 - 20 °C

2: 1.85 g / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

3: 80 percent / pTSA / acetone / 5 h / 20 °C

4: 88 percent / sodium azide / dimethylformamide / 24 h / 110 °C

5: 91 percent / hydrogen / Lindlar's catalyst / methanol / 4 h / 20 °C / 760 Torr

6: 86 percent / pyridine / 3 h / 0 - 20 °C

7: 80 percent / FeCl₃*6H₂O / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; triethylsilane; sodium azide; boron trifluoride diethyl etherate; hydrogen; iron(III) chloride; toluene-4-sulfonic acid; Lindlar's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2006.08.035