527-52-6

Basic information

• Product Name: D-(+)-DIGITOXOSE
• Synonyms: D-(+)-DIGITOXOSE;D-DIGITOXOSE;DIGITOXOSE;DIGITOXOSE, D-(+)-;2,6-DI-DEOXY-D-RIBOHEXOSE;2,6-DIDEOXY-D-RIBOSE;2,6-DI-DEOXY-D-RIBOTHEXOSE;2,6-dideoxy-D-altrose
• CAS NO: 527-52-6
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.16
• EINECS: 208-416-6
• Product Categories: Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 527-52-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 98-100 °C
• Boiling Point: 188.74°C (rough estimate)
• Flash Point: 147.4 °C
• Appearance: /
• Density: 1.0610 (rough estimate)
• Vapor Pressure: 2.64E-05mmHg at 25°C
• Refractive Index: 1.4320 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 13.72±0.20(Predicted)
• CAS DataBase Reference: D-(+)-DIGITOXOSE(CAS DataBase Reference)
• NIST Chemistry Reference: D-(+)-DIGITOXOSE(527-52-6)
• EPA Substance Registry System: D-(+)-DIGITOXOSE(527-52-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 527-52-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 527-52-6 differently. You can refer to the following data:
1. A derivative of D-ribo-Hexonic acid that is metabolized in the liver. It inhibits glucose-stimulated insulin release.
2. D-Digitoxose is a derivative of D-ribo-Hexonic acid that is metabolized in the liver. It inhibits glucose-stimulated insulin release.

Purification Methods

Crystallise D(+)-digitoxose from MeOH/Et2O, Et2O, EtOAc, EtOAc/Et2O/pet ether or Me2CO/Et2O and dry it over P2O5/vacuum. It has [] D +45.2o (6minutes) mutarotating to +50.2o (16hours constant) (c 1.65, H2O). [Gut & Prins Helv Chim Acta 20 1229 1947, Bollinger & Ulrich Helv Chim Acta 35 93 1952, NMR of derivs: Tsukamoto et al. J Chem Soc, Perkin Trans 1 2621 1988, Beilstein 1 IV 4191.]

InChI:InChI=1/C6H12O4/c1-3-6(9)4(7)2-5(8)10-3/h3-9H,2H2,1H3/t3-,4+,5-,6-/m1/s1

Synthetic route

methyl 2,6-dideoxy-α-D-ribo-hexopyranoside (4092-45-9, 13322-79-7, 17676-16-3, 17676-19-6, 19131-10-3, 19131-11-4, 33985-35-2, 40878-56-6, 53293-94-0, 56733-47-2, 62346-15-0, 71305-70-9, 72204-04-7, 77210-24-3, 78853-88-0, 92007-64-2, 133814-52-5, 139756-72-2) → D-digitxose (527-52-6)

Conditions	Yield
With sulfuric acid

sulfuric acid (7664-93-9) + (2R,3S,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol (69515-54-4) → D-digitxose (527-52-6) + compound C6H12O4

digitoxigen (β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside (19855-40-4) + aqueous methanol. sulfuric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + digilanidobiose

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A (17575-20-1) + diluted aq.-ethanolic sulfuric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + digilanidobiose

Conditions	Yield
at 40℃; anschliessendes Behandeln mit verd. wss. Schwefelsaeure;

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + water (7732-18-5) + gitoxin (4562-36-1) → D-digitxose (527-52-6) + gitoxigenin

hydrogenchloride (7647-01-0) + gitoxigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-digitoxopyranoside (19855-39-1) → D-digitxose (527-52-6) + gitoxigenin + digilanidobiose

O4'-β-Cellobiosyl-gitoxin (121576-17-8) + aqueous methanol. sulfuric acid → D-digitxose (527-52-6) + gitoxin + digilanidotriose

Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A (17575-20-1) + diluted aqueous methanol. hydrochloric acid → D-digitxose (527-52-6) + (+)-digitoxigenin (143-62-4) + O3-acetyl-digilanidobiose

Conditions	Yield
anschliessendes Behandeln mit verd. wss. Salzsaeure;

(2R)-2r-methyl-3,4-dihydro-2H-pyran-3t,4t-diol → D-digitxose (527-52-6)

Conditions	Yield
With sulfuric acid

Methyl 2,3-anhydro-4,6-bis-α-D-allopyranoside (71811-64-8) → D-digitxose (527-52-6) + potassium iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; tetrahydrofuran 2: aqueous sulfuric acid View Scheme

methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside (33650-60-1) → D-digitxose (527-52-6) + potassium iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: barium hydroxide; aqueous methanol 2: aqueous sulfuric acid View Scheme

methyl 2,6-dideoxy-4-O-p-tolylsulfonyl-α-D-ribo-hexapyranoside (107908-90-7) → D-digitxose (527-52-6) + potassium iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous methanol; sodium-amalgam 2: aqueous sulfuric acid View Scheme

methyl 2,3-anhydro-α-D-allopyranoside (3257-61-2) → D-digitxose (527-52-6) + potassium iodide

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: lithium alanate; tetrahydrofuran 3: aqueous sulfuric acid View Scheme

syriacoside M → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + D-glucose (50-99-7) + ikemagenin

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside N → D-digitxose (527-52-6) + D-symarose (13089-76-4) + D-glucose (50-99-7) + ikemagenin

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside O → D-digitxose (527-52-6) + D-symarose (13089-76-4) + D-glucose (50-99-7) + 5α,6-dihydroikemagenin (272444-27-6)

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside P (1173896-43-9) → D-digitxose (527-52-6) + D-symarose (13089-76-4) + D-glucose (50-99-7) + 12-O-tigloylisolineolon

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside Q → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + D-glucose (50-99-7) + ikemagenin

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside A → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + ikemagenin

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 60℃; for 0.75h;

syriacoside B → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + ikemagenin

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 60℃; for 0.75h;

syriacoside C → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + ikemagenin

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 60℃; for 0.75h;

syriacoside D → D-digitxose (527-52-6) + D-symarose (13089-76-4) + ikemagenin

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 98℃; for 1h;

syriacoside H → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + ikemagenin

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 60℃; for 0.75h;

syriacoside I → D-digitxose (527-52-6) + D-symarose (13089-76-4) + ikemagenin

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 60℃; for 0.75h;

(3β,12β,14β,17α)-3-{[2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-12-{[(2E)-3-phenylprop-2-enoyl]oxy}pregn-5-en-20-yl 3-methylbutanoate (1206547-23-0) → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + 12-O-cinnamoyl-20-O-isovaleeroylsarcostin

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃; for 1.5h;

(3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate (1206547-24-1) → qingyangshengenin + D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + L-cymarose (32791-73-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃; for 1.5h;

(3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate (1206547-25-2) → qingyangshengenin + D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + L-cymarose (32791-73-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃; for 1.5h;

(3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl 4-hydroxybenzoate (1206547-26-3) → qingyangshengenin + D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + L-cymarose (32791-73-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃; for 1.5h;

(3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-α-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl (2E)-3,4-dimethylpent-2-enoate (1206547-27-4) → D-digitxose (527-52-6) + D-oleandrose (90-56-2, 579-04-4, 4432-92-2, 6786-76-1, 13089-76-4, 13089-77-5, 13484-14-5, 22252-39-7, 23457-90-1, 32791-73-4, 85761-09-7, 120787-85-1, 18607-77-7) + D-symarose (13089-76-4) + L-cymarose (32791-73-4) + caudatin

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol; water at 60℃; for 1.5h;

D-digitxose (527-52-6) + ethanethiol (75-08-1) → 2,6-dideoxy-D-ribo-hexose diethyl dithioacetal (13051-82-6)

Conditions	Yield
With hydrogenchloride; water at 0℃; for 3h;	81%
With hydrogenchloride

D-digitxose (527-52-6) + 2-naphthylsulfonyl hydrazide (10151-46-9) → naphthalene-2-sulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

D-digitxose (527-52-6) + 4-nitrobenzenesulfonohydrazide (2937-05-5) → 4-nitro-benzenesulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

D-digitxose (527-52-6) + 4-biphenylsulfonyl hydrazide (855276-86-7) → biphenyl-4-sulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

D-digitxose (527-52-6) + 5-nitro-naphthalene-2-sulfonic acid hydrazide → 5-nitro-naphthalene-2-sulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

D-digitxose (527-52-6) + 8-nitro-naphthalene-2-sulfonic acid hydrazide → 8-nitro-naphthalene-2-sulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

D-digitxose (527-52-6) + 4'-nitro-biphenyl-4-sulfonic acid hydrazide (875855-53-1) → 4'-nitro-biphenyl-4-sulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide) (109535-90-2)

D-digitxose (527-52-6) → 1,5-Dideoxy-L-ribo-hexitol (62083-73-2, 95191-22-3, 116563-04-3)

Conditions	Yield
With sodium amalgam in saurer Loesung;
With sodium tetrahydroborate In N,N-dimethyl-formamide

D-digitxose (527-52-6) → D-ribo-3,4,5-trihydroxy-hexanoic acid (24160-48-3)

Conditions	Yield
With water; bromine

D-digitxose (527-52-6) → L-erythro-2.3-dihydroxy-glutaric acid (33054-05-6, 34321-30-7, 34693-49-7, 82864-78-6) + meso-tartaric acid (147-73-9)

Conditions	Yield
With nitric acid at 90℃;

D-digitxose (527-52-6) → meso-tartaric acid (147-73-9)

Conditions	Yield
With nitric acid

D-digitxose (527-52-6) → 3,4,5-trihydroxy-hexanal oxime

Conditions	Yield
With hydroxylamine hydrochloride; water; sodium carbonate

D-digitxose (527-52-6) → 2,4,5,6-tetrahydroxy-heptanoic acid

Conditions	Yield
With hydrogen cyanide durch Verseifung der entstehenden Nitril mit Baryt;

D-digitxose (527-52-6) → ribo-2,6-dideoxy-hexonic acid-(N'-phenyl-hydrazide) (20561-87-9, 20561-91-5, 20561-92-6, 73491-12-0, 83108-11-6, 95103-71-2)

Conditions	Yield
With water; bromine Eindampfen der von Bromwasserstoff und Brom befreiten Loesung bei 50grad zum Sirup, diesen in Alkohol loesen und Hinzugeben von Phenylhydrazin; levorotatory substance;

D-digitxose (527-52-6) + acetic anhydride (108-24-7) → (4S,5R,6R)-6-methyltetrahydro-2H-pyran-2,4,5-triyl triacetate (67335-77-7)

Conditions	Yield
With pyridine

D-digitxose (527-52-6) + benzoyl chloride (98-88-4) → tri-O-benzoyl-β-D-ribo-2,6-dideoxy-hexopyranose (104652-04-2)

Conditions	Yield
With pyridine

D-digitxose (527-52-6) + 4-nitro-benzoyl chloride (122-04-3) → tris-O-(4-nitro-benzoyl)-β-D-ribo-2,6-dideoxy-hexopyranose] (69881-26-1)

Conditions	Yield
With pyridine

D-digitxose (527-52-6) + 1,2-diamino-benzene (95-54-5) → D-ribo-1-(1H-benzimidazol-2-yl)-pentane-2,3,4-triol

Conditions	Yield
With copper diacetate; acetic acid

D-digitxose (527-52-6) + 4-phenylazo-benzenesulfonic acid hydrazide (3420-00-6) → 4-phenylazo-benzenesulfonic acid-(D-ribo-2,6-dideoxy-hexitol-1-ylidenehydrazide)

Conditions	Yield
With acetonitrile

Upstream product

• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 4562-36-1 gitoxin 
• 19855-39-1 gitoxigenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-digitoxopyranoside 
• 121576-17-8 O^4'-β-Cellobiosyl-gitoxin 
• 17575-20-1 Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A 
• 77210-24-3 methyl 2,6-dideoxy-α-D-xylo-hexopyranoside 
• 14711-68-3 methyl-[bis-O-(toluene-4-sulfonyl)-α-D-xylo-2,6-dideoxy-hexopyranoside] 
• 897959-06-7 methyl-[tris-O-(toluene-4-sulfonyl)-α-D-xylo-2-deoxy-hexopyranoside] 
• 67308-47-8 methyl-(α-D-xylo-2-deoxy-hexopyranoside) 
• 104048-44-4 (1S,2R)-(S)-1-(4,5-Dihydro-isoxazol-5-yl)-propane-1,2-diol 
• 104048-44-4 (1R,2S)-(S)-1-(4,5-Dihydro-isoxazol-5-yl)-propane-1,2-diol 

Downstream Products

• 24160-48-3 D-ribo-3,4,5-trihydroxy-hexanoic acid 
• 33054-05-6 L-erythro-2.3-dihydroxy-glutaric acid 
• 147-73-9 meso-tartaric acid 
• 20561-87-9 ribo-2,6-dideoxy-hexonic acid-(N'-phenyl-hydrazide) 
• 291282-23-0 C₃₁H₄₀O₃S₂ 
• 102235-57-4 3,4,5-Tri-O-benzyl-2,6-didesoxy-D-ribo-aldehydo-hexose 
• 87-69-4 tartaric acid 
• 69881-26-1 tris-O-(4-nitro-benzoyl)-β-D-ribo-2,6-dideoxy-hexopyranose] 
• 104652-04-2 tri-O-benzoyl-β-D-ribo-2,6-dideoxy-hexopyranose 
• 67335-77-7 (4S,5R,6R)-6-methyltetrahydro-2H-pyran-2,4,5-triyl triacetate 

Relevant articles and documents

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