N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol
CAS No.:1354483-36-5
Molecular Formula:C₂₃H₃₇NO₈S
Molecular Weight:487.615
Hs Code.:

Synonyms:N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

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Chemical Property of N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

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Technology Process of N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

There total 6 articles about N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol 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: 88.0%

: N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)-hex-2-enyl]-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol

: 1354483-36-5
N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

Guidance literature:: With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 5.5h;
DOI:10.1080/07328303.2011.610544

Reference yield:

: 1354483-30-9
(1R)-1-C-allyl-N-naphth-2-ylmethyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol

: 1354483-36-5
N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

Guidance literature:: Multi-step reaction with 4 steps

1: methanol / dichloromethane

2: triethylamine / dichloromethane / 3.5 h / 0 - 20 °C

3: Hoveyda-Grubbs catalyst second generation / dichloromethane / 23 h / Reflux

4: hydrogenchloride; palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol; water / 5.5 h / 20 °C

With hydrogenchloride; methanol; Hoveyda-Grubbs catalyst second generation; palladium 10% on activated carbon; hydrogen; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1080/07328303.2011.610544

Reference yield:

: 1-C-allyl-2,3,4-tri-O-benzyl-1-naphth-2-ylmethylamino-1-deoxy-D-xylitol

: 1354483-36-5
N-(tert-butoxycarbonyl)-(1R)-1-C-[6-(toluene-4-sulfonyloxy)hexyl]-1,5-dideoxy-1,5-imino-D-xylitol

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine; methanesulfonyl chloride / 4 h / 100 °C / Molecular sieve

2: methanol / dichloromethane

3: triethylamine / dichloromethane / 3.5 h / 0 - 20 °C

4: Hoveyda-Grubbs catalyst second generation / dichloromethane / 23 h / Reflux

5: hydrogenchloride; palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol; water / 5.5 h / 20 °C

With pyridine; hydrogenchloride; methanol; Hoveyda-Grubbs catalyst second generation; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1080/07328303.2011.610544