200399-47-9

Basic information

• Product Name: SALACINOLEXTRACT
• Synonyms: SALACINOLEXTRACT;(1S,2R,3S,4S)-1-[(2S,3S)-2,4-Dihydroxy-3-(sulfooxy)butyl]tetrahydro-3,4-dihydroxy-2-(hydroxyMethyl)thiopheniuM Inner Salt;1,4-Dideoxy-1,4-[(S)-[(2S,3S)-2,4-dihydroxy-3-(sulfooxy)butyl]episulfoniuMylidene]-D-arabinitol Inner Salt
• CAS NO: 200399-47-9
• Molecular Formula: C₉H₁₈O₉S₂
• Molecular Weight: 334.36382
• Mol File: 200399-47-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: SALACINOLEXTRACT(CAS DataBase Reference)
• NIST Chemistry Reference: SALACINOLEXTRACT(200399-47-9)
• EPA Substance Registry System: SALACINOLEXTRACT(200399-47-9)

Safety Data

• Hazardous Substances Data: 200399-47-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 200399-47-9 differently. You can refer to the following data:
1. SALACINOLEXTRACT is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.
2. Salacinol is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.

InChI:InChI=1/C9H18O9S2/c10-1-7(18-20(15,16)17)5(12)3-19-4-6(13)9(14)8(19)2-11/h5-14H,1-4H2/t5-,6-,7+,8-,9+,19?/m1/s1

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 → (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 (200399-47-9)

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

2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (942610-80-2) → (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 (200399-47-9)

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

1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol (438576-21-7) → (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 (200399-47-9)

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 → (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 (200399-47-9)

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 → (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 (200399-47-9)

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

3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7) → (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 (200399-47-9)

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

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol (187590-77-8) → (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 (200399-47-9)

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

(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol (160882-26-8) → (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 (200399-47-9)

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

(2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydrothiophene (635316-05-1) → (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 (200399-47-9)

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 → (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 (200399-47-9)

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

(4S,5S)-4-(((1S,2R,3S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)meth yl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylamine; methanol / 1 h / 25 °C 2: 20% palladium hydroxide-activated charcoal; hydrogen / acetic acid / 2 h / 50 °C View Scheme

(2S,3S)-4-[((1R,2R,3S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium-1-yl)]-1,3-dihydroxybutan-2-ylsulfate → (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 (200399-47-9)

Conditions	Yield
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid at 50℃; for 2h;
With 20% palladium hydroxide-activated charcoal; hydrogen In acetic acid at 50℃; for 2h;
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid at 50℃; for 2h;

(4S,5S)-4-(((1S,2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-1,3-dioxan-5-yl sulfate → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylamine / methanol / 3 h / 25 °C 2: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: diethylamine; methanol / 3 h / 25 °C 2: water; trifluoroacetic acid / 2 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: diethylamine / methanol / 3 h / 25 °C 2: trifluoroacetic acid / water / 2 h / 25 °C View Scheme

(2S,3S)-4-((1R,2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydro-1H-thiophene-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate → (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 (200399-47-9)

Conditions	Yield
With trifluoroacetic acid In water at 25℃; for 2h;
With water; trifluoroacetic acid at 25℃; for 2h;
With trifluoroacetic acid In water at 25℃; for 2h;

(4S,5S)-2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(((2R,3 S,4 S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium-1-yl)methyl)-1,3-dioxan-5-yl sulfate → (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 (200399-47-9)

Conditions	Yield
With diethylamine In water; ethyl acetate at 25℃; for 9h;	1.32 g
With water; diethylamine In ethyl acetate at 25℃; for 9h;
With diethylamine In water; ethyl acetate at 25℃; for 9h; Reagent/catalyst; Solvent; Temperature;

(1S,4S,7S)-3-methoxy-2-oxa-5-thiabicyclo[2.2.1]heptan-7-yl 4-methylbenzoate → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 1 h / 50 °C 1.2: 1.67 h / 5 - 25 °C 2.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 3.2: 6 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 5.1: diethylamine / methanol / 3 h / 25 °C 6.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 1 h / 50 °C 1.2: 1.67 h / 5 - 25 °C 2.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 5 °C 3.2: 3 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 5.1: diethylamine / methanol / 1 h / 25 °C 6.1: hydrogen; acetic acid; 20% palladium hydroxide-activated charcoal / 2 h / 50 °C View Scheme
Multi-step reaction with 6 steps 1.1: water; hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 1.2: 1.67 h / 5 - 25 °C 2.1: methanol; sodium methylate / tetrahydrofuran / 4 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 3.2: 6 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 5.1: diethylamine; methanol / 3 h / 25 °C 6.1: water; trifluoroacetic acid / 2 h / 25 °C View Scheme
Multi-step reaction with 6 steps 1.1: water; hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 1.2: 1.67 h / 5 - 25 °C 2.1: methanol; sodium methylate / tetrahydrofuran / 4 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 5 °C 3.2: 3 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 5.1: diethylamine; methanol / 1 h / 25 °C 6.1: 20% palladium hydroxide-activated charcoal; hydrogen / acetic acid / 2 h / 50 °C View Scheme

(2R,3S,4S)-4-hydroxy-2-(hydroxymethyl)tetrahydrothiophene-3-yl 4-methylbenzoate → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 2.2: 6 h / 0 - 25 °C 3.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 4.1: diethylamine / methanol / 3 h / 25 °C 5.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 5 °C 2.2: 3 h / 0 - 25 °C 3.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 4.1: diethylamine / methanol / 1 h / 25 °C 5.1: hydrogen; acetic acid; 20% palladium hydroxide-activated charcoal / 2 h / 50 °C View Scheme
Multi-step reaction with 5 steps 1.1: methanol; sodium methylate / tetrahydrofuran / 4 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 2.2: 6 h / 0 - 25 °C 3.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 4.1: diethylamine; methanol / 3 h / 25 °C 5.1: water; trifluoroacetic acid / 2 h / 25 °C View Scheme

(1S,4S,7S)-3-methoxy-2-oxa-5-thiabicyclo[2.2.1]heptane-7-ol → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: tetrabutyl-ammonium chloride; sodium hydroxide / water; toluene / 3 h / 10 - 25 °C 2.1: hydrogenchloride / tetrahydrofuran; water / 1 h / 50 °C 2.2: 1.67 h / 5 - 25 °C 3.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 4.2: 6 h / 0 - 25 °C 5.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 6.1: diethylamine / methanol / 3 h / 25 °C 7.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 7 steps 1.1: tetrabutyl-ammonium chloride; sodium hydroxide / water; toluene / 3 h / 10 - 25 °C 2.1: hydrogenchloride / tetrahydrofuran; water / 1 h / 50 °C 2.2: 1.67 h / 5 - 25 °C 3.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 5 °C 4.2: 3 h / 0 - 25 °C 5.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 6.1: diethylamine / methanol / 1 h / 25 °C 7.1: hydrogen; acetic acid; 20% palladium hydroxide-activated charcoal / 2 h / 50 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydroxide; tetrabutyl-ammonium chloride / water; toluene / 10 °C 1.2: 3 h / 15 - 25 °C 2.1: hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 2.2: 1.5 h / 5 - 25 °C 3.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 4.2: 6 h / 0 - 25 °C 5.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 6.1: diethylamine / methanol / 3 h / 25 °C 7.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydroxide; tetrabutyl-ammonium chloride / water; toluene / 10 °C 1.2: 3 h / 15 - 25 °C 2.1: hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 2.2: 1.5 h / 5 - 25 °C 3.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 5 °C 4.2: 3 h / 0 - 25 °C 5.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 6.1: diethylamine / methanol / 1 h / 25 °C 7.1: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / 2 h / 50 °C View Scheme

(1S,4S,7S)-3-methoxy-2-oxa-5-thiabicyclo[2.2.1]heptan-7-yl 4-methylbenzoate → (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 (200399-47-9)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 1.2: 1.5 h / 5 - 25 °C 2.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 3.2: 6 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 13 h / 70 °C 5.1: diethylamine / methanol / 3 h / 25 °C 6.1: trifluoroacetic acid / water / 2 h / 25 °C View Scheme
Multi-step reaction with 6 steps 1.1: hydrogenchloride / tetrahydrofuran / 1 h / 50 °C 1.2: 1.5 h / 5 - 25 °C 2.1: sodium methylate / tetrahydrofuran; methanol / 4 h / 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 - 5 °C 3.2: 3 h / 0 - 25 °C 4.1: 2,6-dimethylpyridine / acetone / 24 h / 70 °C 5.1: diethylamine / methanol / 1 h / 25 °C 6.1: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / 2 h / 50 °C View Scheme

methanol (67-56-1) + (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 (200399-47-9) → 1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,3,4-trihydroxybutyl]episulfonioylidene}-D-arabinitol methyl sulfate

Conditions	Yield
With hydrogenchloride at 40℃; for 3h;	93%
With hydrogenchloride for 1h; Reflux;	88%
With hydrogenchloride at 45℃; for 3h;	86%

(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 (200399-47-9) → (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol (160882-26-8)

Conditions	Yield
With NaPMe In methanol for 3h; Heating;	44%

Upstream product

• 160882-26-8 (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 
• 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 
• 438576-21-7 1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol 
• 635316-05-1 (2R,3S,4S)-3,4-bis((4-methoxybenzyl)oxy)-2-(((4-methoxybenzyl)oxy)methyl)tetrahydrothiophene 
• 187590-77-8 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol 
• 160882-25-7 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 

Relevant articles and documents

Improved syntheses of the naturally occurring glycosidase inhibitor salacinol

Improved syntheses of the naturally occurring sulfonium ion, salacinol are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 Diabetes. The synthetic strategy relies on the nucleophilic attack of 2,3,5-triO-benzyl- or 2,3,5-tri-O-p-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol at the least hindered carbon of benzylidene-protected L-erythritol-1,3-cyclic sulfate in 1,1,1,3,3,3-hexafluoro-2-propanol as solvent. The reactions are compared to those with the benzyl-protected L-erythritol-1,3-cyclic sulfate and also to those in acetone and 2-propanol. Excellent yields are obtained for the reactions with the benzylidene-protected cyclic sulfate. The synthetic route employing p-methoxybenzyl ether protecting groups is advantageous since all protecting groups in the adduct may be removed with trifluoroacetic acid to yield salacinol, thereby obviating the problematic deprotection of benzyl ethers by hydrogenolysis.

COMPOUNDS USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE SAME, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP

PROBLEM TO BE SOLVED: To provide novel compounds useful for manufacturing salacinol, a method for manufacturing the compounds, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. SOLUTION: A compound represented by formula (7a) is a compound useful for manufacturing salacinol. (In the formula, R4ba is a p-toluoyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity

De-O-sulfonated analogs (10a, Y- = CH3OSO3 and 10b, Y- = Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y- = CH3OSO3) with l-thiosugar moiety (1,4-dideoxy-1,4-epithio-l-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent α-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of 1a against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity.