2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

Base Information

Chemical Name:2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol
CAS No.:1068608-25-2
Molecular Formula:C₄₈H₆₉N₃O₇S
Molecular Weight:832.158
Hs Code.:

Synonyms:2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

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Chemical Property of 2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

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Technology Process of 2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

There total 12 articles about 2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol 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: 73.0%

: 1042397-88-5
2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose

: 1068608-22-9
2-azido-3,4-O-isopropylidene-D-ribo-1-iodo-3,4-octadecanediol

: 1068608-25-2
2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

Guidance literature:: With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 24h; pH=8.5; Inert atmosphere;
DOI:10.1021/ol8019555

Reference yield:

: 88303-25-7
tetradecylmagnesium bromide

: 1068608-25-2
2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

Guidance literature:: Multi-step reaction with 10 steps

1: tetrahydrofuran

2: pyridine

3: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

4: sodium methylate / methanol

5: toluene-4-sulfonic acid / methanol; dichloromethane

6: sodium azide / N,N-dimethyl-formamide / Heating

7: toluene-4-sulfonic acid

8: pyridine

9: lithium iodide / N,N-dimethyl-formamide

10: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / ethyl acetate

With pyridine; sodium azide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: |Grignard Reaction / 3: |Mitsunobu Displacement;
DOI:10.3998/ark.5550190.0014.224

Reference yield:

: 117168-59-9
(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

: 1068608-25-2
2-azido-3,4-O-isopropylidene-1-S-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-D-ribo-3,4-octadecanediol

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid

2: pyridine

3: lithium iodide / N,N-dimethyl-formamide

4: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / ethyl acetate

With pyridine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium iodide; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.3998/ark.5550190.0014.224