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200399-47-9

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Basic Information

Molecular Structure:
CAS No.:	200399-47-9
Name:	SALACINOLEXTRACT
Article Data:	5

Formula:	C₉H₁₈O₉S₂
Molecular Weight:	334.369
Synonyms:	SALACINOL;
PSA:	218.98000
LogP:	-3.45510

Synthetic route

: 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-{[(2S,3S)-2,4-benzylidenedioxy-3-(sulfooxy)butyl]-episulfoniumylidene}-D-arabinitol inner salt

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With trifluoroacetic acid at 20℃; for 0.5h;	86%

: 942610-80-2
2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal at 50℃; for 5h;	82%

: 438576-21-7
1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With hydrogenchloride at 40℃; for 4h;	74%

: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{[(2S,3S)-2,4-benzylidenedioxy-3-(sulfooxy)butyl]-episulfoniumylidene}-D-arabinitol inner salt

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With hydrogen; palladium dihydroxide In water; acetic acid	65%

: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{[(2S,3S)-2,4-di(benzyloxy)-3-(sulfooxy)butyl]-episulfoniumylidene}-D-arabinitol inner salt

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With hydrogen; palladium dihydroxide In water; acetic acid	65%

: 160882-25-7
3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C 2: 99 percent / potassium carbonate / various solvent(s) / 6 h / Heating 3: 82 percent / aq. acetic acid; hydrogen / Pd/C / 5 h / 50 °C View Scheme

: 187590-77-8
1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / potassium carbonate / various solvent(s) / 6 h / Heating 2: 82 percent / aq. acetic acid; hydrogen / Pd/C / 5 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 94 percent / K2CO3 / various solvent(s) / 14 h / Heating 2: 65 percent / H2 / Pd(OH)2 / acetic acid; H2O View Scheme
Multi-step reaction with 2 steps 1: 45 percent / K2CO3 / various solvent(s) / 14 h / Heating 2: 65 percent / H2 / Pd(OH)2 / acetic acid; H2O View Scheme

: 160882-26-8
(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / NaH / tetrahydrofuran / 13 h / 20 - 55 °C 2: 100 percent / K2CO3 / various solvent(s) / Heating 3: 86 percent / aq. trifluoroacetic acid / 0.5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 1.2: 6 h / 0 - 25 °C 2.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 3.1: diethylamine / methanol / 3 h / 25 °C 4.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 5 °C 1.2: 3 h / 0 - 25 °C 2.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 3.1: diethylamine / methanol / 1 h / 25 °C 4.1: hydrogen; acetic acid; 20% palladium hydroxide-activated charcoal / 2 h / 50 °C View Scheme

: 635316-05-1
(2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydrothiophene

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / K2CO3 / various solvent(s) / Heating 2: 86 percent / aq. trifluoroacetic acid / 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 2: diethylamine / methanol / 3 h / 25 °C 3: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 2: diethylamine; methanol / 3 h / 25 °C 3: water; trifluoroacetic acid / 2 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 2: diethylamine / methanol / 3 h / 25 °C 3: trifluoroacetic acid / water / 2 h / 25 °C View Scheme

: (4S,5S)-4-(((2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium)-1-yl)methyl-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate

: 200399-47-9
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate

Conditions	Yield
With diethylamine In water; ethyl acetate at 25℃; for 0.833333h; Reagent/catalyst; Solvent;	1.05 g
With water; diethylamine In ethyl acetate at 25℃; for 0.833333h; Reagent/catalyst; Temperature; Solvent;	1.05 g
With diethylamine In water; ethyl acetate at 25℃; for 0.833333h; Reagent/catalyst; Solvent; Temperature;	1.05 g

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