N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

Base Information

Chemical Name:N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride
CAS No.:1425499-48-4
Molecular Formula:C₁₅H₂₉NO₃*ClH
Molecular Weight:307.861
Hs Code.:

Synonyms:N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

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Chemical Property of N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

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Technology Process of N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

There total 9 articles about N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride 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: 90.0%

: 111-86-4
n-Octylamine

: 1425499-47-3
3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

: 1425499-48-4
N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

Guidance literature:: n-Octylamine; 3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide; In acetonitrile; at 60 ℃; for 22h; Sealed tube;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 2.5h;
DOI:10.1016/j.carres.2012.12.010

Reference yield:

: 488-73-3
(+)-proto-quercitol

: 1425499-48-4
N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

Guidance literature:: Multi-step reaction with 9 steps

1.1: camphor-10-sulfonic acid / acetone / 19 h / 20 °C

2.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 4.5 h / 0 - 20 °C

3.1: pyridinium p-toluenesulfonate / methanol / 23 h / 4 °C

4.1: pyridine / 21 h / 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 21 h / 4 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; bromine / tetrachloromethane / 0.5 h / 20 °C

7.1: sodium borohydrid / water; N,N,N,N,N,N-hexamethylphosphoric triamide / 3 h / 20 °C

8.1: sodium methylate / methanol / 21 h / 4 - 20 °C

9.1: acetonitrile / 22 h / 60 °C / Sealed tube

9.2: 2.5 h / 20 °C

With pyridine; n-butyllithium; sodium borohydrid; camphor-10-sulfonic acid; bromine; sodium methylate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; dimethyl sulfoxide; acetone; acetonitrile; 5.2: |Wittig-Horner Reaction;
DOI:10.1016/j.carres.2012.12.010

Reference yield:

: 1425499-45-1
2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

: 1425499-48-4
N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 21 h / 4 - 20 °C

2.1: acetonitrile / 22 h / 60 °C / Sealed tube

2.2: 2.5 h / 20 °C

With sodium methylate; In methanol; acetonitrile;
DOI:10.1016/j.carres.2012.12.010