(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran
CAS No.:844837-51-0
Molecular Formula:C₃₄H₃₅N₃O₄S
Molecular Weight:581.736
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

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Chemical Property of (2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

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Technology Process of (2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

There total 2 articles about (2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran 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: 47.0%

: 106-45-6
para-thiocresol

: 468065-27-2
perbenzyl-perazidotobramyicn

: 844837-51-0
(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1002/anie.200460558

Reference yield:

: (2S,3R,5S,6R)-4-Azido-2-[(2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

: 844837-51-0
(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: NaH; TBAI / dimethylformamide

2: 47 percent / BF₃*Et₂O / CH₂Cl₂

With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200460558

Reference yield:

: 844837-51-0
(2R,3S,4S,5R,6R)-4-Azido-3,5-bis-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran

: 4-amino-2-{5-amino-2-aminomethyl-6-[4,6-diamino-3-(3-amino-6-aminomethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-4-hydroxy-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1: N-iodosuccinimide; TfOH; 4 Angstroem molecular sieves / CH₂Cl₂ / -45 °C

2: NaOMe / methanol

3: NaH; TBAI / dimethylformamide

4: benzenesulfinylpiperidine; Tf₂O; 4 Angstroem molecular sieves / CH₂Cl₂ / -45 - -20 °C

5: Raney Ni; hydrazine / ethanol; dioxane / 20 °C

6: H₂; aq. HCl / Pd(OH)2 / methanol / 20 °C

With hydrogenchloride; N-iodo-succinimide; 1-benzenesulfinyl piperidine; trifluorormethanesulfonic acid; trifluoromethylsulfonic anhydride; 4 A molecular sieve; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; nickel; sodium hydride; hydrazine; palladium dihydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200460558