(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

Base Information

Chemical Name:(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate
CAS No.:1454797-13-7
Molecular Formula:C₄₈H₅₀O₁₀S₂
Molecular Weight:851.051
Hs Code.:

Synonyms:(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

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Chemical Property of (2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

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Technology Process of (2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

There total 4 articles about (2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate 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%

: 1454797-11-5
(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diol

: 124-63-0
methanesulfonyl chloride

: 1454797-13-7
(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-05-7
(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

: 1454797-13-7
(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; tert-butyl alcohol; water / 20 °C / Inert atmosphere

2: sodium periodate / water; acetonitrile / 5 h / 20 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 1.25 h / 0 °C / Inert atmosphere

4: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-09-1
(2R,3R,4S)-1,3,4-tris(benzyloxy)-5-oxo-6-(trityloxy)hexan-2-yl formate

: 1454797-13-7
(2R,3S,4S,5S)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 1.25 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo401613v