[ CAS No. 367-93-1 ] {[proInfo.proName]}

Name: 367-93-1|(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol|98%
Brand: Ambeed
SKU: A193402
Price: 5.0 USD
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2D 3D

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Quality Control of [ 367-93-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 367-93-1 ]

SDS Specification

Alternatived Products of [ 367-93-1 ]

Product Details of [ 367-93-1 ]

CAS No. :	367-93-1	MDL No. :	MFCD00063273
Formula :	C₉H₁₈O₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BPHPUYQFMNQIOC-NXRLNHOXSA-N
M.W :	238.30	Pubchem ID :	656894
Synonyms :		Chemical Name :	(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triol

Calculated chemistry of [ 367-93-1 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	4.0
Molar Refractivity :	56.59
TPSA :	115.45 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	-1.26
Log Po/w (WLOGP) :	-1.07
Log Po/w (MLOGP) :	-1.34
Log Po/w (SILICOS-IT) :	-0.79
Consensus Log Po/w :	-0.52

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.33
Solubility :	113.0 mg/ml ; 0.472 mol/l
Class :	Very soluble
Log S (Ali) :	-0.67
Solubility :	51.2 mg/ml ; 0.215 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	1.1
Solubility :	2990.0 mg/ml ; 12.5 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.78

Safety of [ 367-93-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 367-93-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 367-93-1 ]
Downstream synthetic route of [ 367-93-1 ]

[ 367-93-1 ] Synthesis Path-Upstream 1~10

1
[ 55692-87-0 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate In methanol at 20℃;	Add 21.4 grams to a 250 ml round bottom flask(52 mmol) isopropyl-β-D thiotetraacetylgalactoside, Then add 50 ml of methanol sodium methoxide solution at pH=10.The reaction is stirred at room temperature for 12 hours to 24 hours.TLC detection,After the reaction is complete, the solvent is removed under reduced pressure.Recrystallization from methanol and acetone gave the desired product 12.1 g.The yield was 98percent.
75.6%	With sodium methylate In methanol	b) 0.774mol isopropyl glucosinolates acetyl galactose added to the 10mol menthol to dissolve, after that added the 0.01mol Sodium methoxide, then after completion of the reaction added the 0.01mol Acetic acid neutralization, after post-processing obtained the 0.756 mol of isopropyl-β-D- thiogalactoside. Yield is 75.6percent. In step a after the post-processing added the drops of 10mol of 0-5 ° C water and stirred for 2 hours, the extracted aqueous layer has been extracted with 5 mol of dichloromethane, the organic phase is separated and the organic phase has washed three times with 10 mol of water, after that organic phase is concentrated, added the 1mol of tert-butyl methyl ether and 2 mol of isohexane mixture crystallized, filtered and dried. In step b the post-treatment is concentrated to get dry, added the 0.2mol ethanol and 1.8mol tert-butyl methyl ether crystal, filtered and dried.
74.3%	With sodium methylate; acetic acid In methanol	0.765 mol of isopropylthioacetylgalactose was added to 10 mol of methanol to dissolve,Add 0.01mol sodium methoxide, the reaction is completed by adding 0.01mol acetic acid and,After the treatment, 0.743 mol of isopropyl -β- D-thiogalactoside was obtained. The yield was 74.3percent.

71.5%

With sodium methylate In methanol

The 0.732mol isopropylthio acetylgalactosamine added 1mol dissolved in methanol, was added sodium methoxide 0.0lmol, the reaction was complete and acetic acid was added 0.0lmol, 0.715mol obtained after treatment isopropyl -β -D- thiogalactoside.The yield was 71.5percent

Reference： [1] Patent: CN103087121, 2018, B, . Location in patent: Paragraph 0013; 0031; 0038-0039
[2] Liebigs Annalen der Chemie, 1983, # 7, p. 1249 - 1256
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 3, p. 839 - 853
[4] Patent: CN103665063, 2016, B, . Location in patent: Paragraph 0032; 0034; 0036
[5] Patent: CN103709209, 2016, B, . Location in patent: Paragraph 0021; 0023
[6] Carbohydrate Research, 1993, vol. 249, # 1, p. 197 - 206
[7] Patent: CN103694284, 2016, B, . Location in patent: Paragraph 0020; 0022

2
[ 10257-28-0 ]
[ 75-33-2 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	Stage #1: at 5 - 10℃; Stage #2: With sodium methylate In methanol	Add 5.5 moles of acetic anhydride and 1 mol of aluminum trichloride at room temperature, add 1 mol of galactose in 12 batches at 5-10 ° C. After completion of the reaction, 1.1 mol of isopropyl mercaptan is added and the reaction is completed to give 0.765 mol Isopropyl thioacetamide;Add 0.765 mol of isopropyl thioacetylated galactose to 10 mol of methanol and add 0.01 mol of sodium methoxide. After completion of the reaction, 0.01 mol of acetic acid was added and subjected to post-treatment to obtain 0.743 mol of isopropyl -β- D- Thiogalactoside. The yield was 74.3percent.In the step a, the mixture was stirred for 10 hours of 0-5 ° C water for 2 hours. The extracted aqueous layer was extracted with 5 mol of methylene chloride. The organic phase was separated and the organic phase was washed three times with 10 mol of water. The organic phase was concentrated, The mixture was crystallized from 1 mol of t-butyl methyl ether and 2 mol of an iso-hexane mixture, filtered and dried.The post-treatment in step b is concentrated to dryness, crystallization of 0.2 mol of ethanol and 1.8 mol of t-butyl methyl ether is added, followed by filtration and drying.

Reference： [1] Patent: CN103694286, 2016, B, . Location in patent: Paragraph 0021-0025

3
[ 25878-60-8 ]
[ 75-33-2 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
45.2%	Stage #1: With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2 h; Stage #2: With sodium methylate In methanol	0.51 moll of pentaacetylgalactose was added to 10 mol of methylene chloride, 0.75 mol of boron trifluoride ether was added, 1.25 mol of isopropyl mercaptan was added at 0-5 ° C, stirred for 2 hours, and the reaction was completed After treatment to obtain 0.453 mol of isopropyl thioacetylated galactose;0.453 mol of isopropyl thioacetylgalactose was dissolved in 10 mol of methanol, 0.01 mol of sodium methoxide was added, and 0.01 mol of acetic acid was added after the completion of the reaction, followed by post-treatment to obtain 0.452 mol of isopropyl -β- D- Thiogalactoside. The yield was 45.2percent.

Reference： [1] Patent: CN103694286, 2016, B, . Location in patent: Paragraph 0041; 0043-0045

4
[ 75-33-2 ]
[ 4163-60-4 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
45.2%	Stage #1: With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2 h; Stage #2: With sodium methylate In methanol	0.51 moll of pentaacetylgalactose was added to 10 mol of methylene chloride, 0.75 mol of boron trifluoride ether was added, 1.25 mol of isopropyl mercaptan was added at 0-5 ° C, stirred for 2 hours, and after completion of the reaction The post-treatment yielded 0.453 mol of isopropylthioacetylated galactose;C) 0.453 mol of isopropyl thioacetylgalactose was dissolved in 10 mol of methanol, 0.01 mol of sodium methoxide was added, and 0.01 mol of acetic acid was added after the completion of the reaction, followed by post-treatment to obtain 0.452 mol of isopropyl -? - D- Thiogalactoside.The yield was 45.2percent.In the step b, the reaction was carried out by adding 10 mol of water at 0-5 ° C for 2 hours, extracting the extracted aqueous layer with 5 mol of methylene chloride, separating the organic phase with 10 mol of water to wash the organic phase three times, separating the organic phase and adding 0.5 mol of t-butyl methyl ether and 1 mol of an iso-hexane mixture, which was filtered and dried.

Reference： [1] Patent: CN103709210, 2016, B, . Location in patent: Paragraph 0027-0029

5
[ 7296-64-2 ]
[ 75-33-2 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
0.5 kg	With potassium acetate In acetic anhydride at 80℃;	1, the first 1kg acetic anhydride into the reaction furnace, plus D-galactose 0.25kg, followed by the catalyst potassium acetate 0.167kgAnd 0.083 kg of isopropyl mercaptan. The catalyst potassium acetate was added in several portions and maintained at a temperature of about 80 ° C to allow sufficient reaction,The reaction time was 24-48 h. The reaction is a slow process that requires complete reaction in order to achieve high purity products.2, the reactants extracted out into the distillation device, the distillation, the temperature at 90 or so, continue to observe the steamDistillation process, until the end of distillation.3, the distillate extracted, and then began to cool down to about 40 , then add methylene chloride 1kg, thenAnd then add water 0.5kg, start mixing reaction, about 30min after the stop, wait 2h, let the reaction fully, and let itDown to room temperature.4, the material extracted, plus water 1kg, stirring 30min stop, static 2h, so that the material fully neutralized. In2h, add water to allow full response, the same method of continuous cleaning three times. A total of about 7h to complete the above steps,Ensure that the pH of the material is around 7.5, extract the material into the reactor, add sodium carbonate 0.08kg, let the pH value of more than 7, and then diluted with tap water,Stirring about 30min or so to stop.6, the furnace material down, the water clean up, add desiccant to dry the water, and then the temperature maintained at 20 leftRight, so that the first refluxing materials and then distillation. When the concentration of dichloromethane, add the temperature to about 50 , until can not be distilleduntil.7, remove all the materials, add ethanol, about 0.5kg, the temperature transferred to about 70 , stirring, and fully reacted, thenAfter the return, full back, reduce losses, to get higher production efficiency.8, the return time is generally controlled at 24h or so, this is a slow process, according to the number of materials, good controlReflux velocity.9, and then put the crystal out, waiting for complete crystallization is complete, this process is about 3-4h, constantly observe the crystal situationAnd the filtration was started after the completion of the crystallization.10, the crystal into the filter, pumping the pumped pounds of ethanol in the crystal, repeat several times until the complete pumpingDry, and then start filtering.11, in ethanol, filtered and drained, and then washed with water, repeat several times to ensure that ethanol is cleaned, and then into theEthanol was drained until ethanol was completely drained.12, and then the crystallization of the water is also drained, and then drying, the temperature control at about 80 , probably with the time2h.13, about 0.5kg about the formal completion of the product.

Reference： [1] Patent: CN105566410, 2016, A, . Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0038

6
[ 4163-60-4 ]
[ 367-93-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 3, p. 839 - 853
[2] Patent: CN103087121, 2018, B,

7
[ 439-03-2 ]
[ 367-93-1 ]

Reference： [1] Carbohydrate Research, 1993, vol. 249, # 1, p. 197 - 206

8
[ 59-23-4 ]
[ 367-93-1 ]

Reference： [1] Patent: CN103694284, 2016, B,
[2] Patent: CN103694284, 2016, B,

9
[ 3947-62-4 ]
[ 367-93-1 ]

Reference： [1] Liebigs Annalen der Chemie, 1983, # 7, p. 1249 - 1256

10
[ 75-33-2 ]
[ 3068-32-4 ]
[ 367-93-1 ]

Reference： [1] Chemische Berichte, 1956, vol. 89, p. 2215,2218

[ 367-93-1 ] Synthesis Path-Downstream 1~88

1
[ 55692-87-0 ]
[ 367-93-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate; In methanol; at 20℃;pH 10;	Add 21.4 grams to a 250 ml round bottom flask(52 mmol) isopropyl-beta-D thiotetraacetylgalactoside, Then add 50 ml of methanol sodium methoxide solution at pH=10.The reaction is stirred at room temperature for 12 hours to 24 hours.TLC detection,After the reaction is complete, the solvent is removed under reduced pressure.Recrystallization from methanol and acetone gave the desired product 12.1 g.The yield was 98%.
75.6%	With sodium methylate; In methanol;	b) 0.774mol isopropyl glucosinolates acetyl galactose added to the 10mol menthol to dissolve, after that added the 0.01mol Sodium methoxide, then after completion of the reaction added the 0.01mol Acetic acid neutralization, after post-processing obtained the 0.756 mol of isopropyl-beta-D- thiogalactoside. Yield is 75.6%. In step a after the post-processing added the drops of 10mol of 0-5 C water and stirred for 2 hours, the extracted aqueous layer has been extracted with 5 mol of dichloromethane, the organic phase is separated and the organic phase has washed three times with 10 mol of water, after that organic phase is concentrated, added the 1mol of tert-butyl methyl ether and 2 mol of isohexane mixture crystallized, filtered and dried. In step b the post-treatment is concentrated to get dry, added the 0.2mol ethanol and 1.8mol tert-butyl methyl ether crystal, filtered and dried.
74.3%	With sodium methylate; acetic acid; In methanol;	0.765 mol of isopropylthioacetylgalactose was added to 10 mol of methanol to dissolve,Add 0.01mol sodium methoxide, the reaction is completed by adding 0.01mol acetic acid and,After the treatment, 0.743 mol of isopropyl -beta- D-thiogalactoside was obtained. The yield was 74.3%.

71.5%

With sodium methylate; In methanol;

Reference： [1]Patent: CN103087121,2018,B .Location in patent: Paragraph 0013; 0031; 0038-0039
[2]Liebigs Annalen der Chemie,1983,p. 1249 - 1256
[3]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853
[4]Patent: CN103665063,2016,B .Location in patent: Paragraph 0032; 0034; 0036
[5]Patent: CN103709209,2016,B .Location in patent: Paragraph 0021; 0023
[6]Carbohydrate Research,1993,vol. 249,p. 197 - 206
[7]Patent: CN103694284,2016,B .Location in patent: Paragraph 0020; 0022
[8]Journal of the American Chemical Society,2020,vol. 142,p. 5498 - 5503

2
[ 712-97-0 ]
[ 367-93-1 ]
C₁₇H₂₁NO₉S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 4290 - 4292

3
[ 367-93-1 ]
[ 847225-62-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853

4
[ 367-93-1 ]
(2S,3R,4S,5S,6R)-4-Allyloxy-2-isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853

5
[ 367-93-1 ]
[ 847225-61-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853

6
[ 367-93-1 ]
[ 847225-70-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853

7
[ 367-93-1 ]
[ 847225-63-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853

8
[ 4163-60-4 ]
[ 367-93-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 839 - 853
[2]Patent: CN103087121,2018,B

9
[ 367-93-1 ]
isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500
[2]Organic Letters,2003,vol. 5,p. 3627 - 3630

10
[ 367-93-1 ]
diosgenyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500
[2]Organic Letters,2003,vol. 5,p. 3627 - 3630

11
[ 367-93-1 ]
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-((4aR,6S,7R,8S,8aR)-8-hydroxy-6-isopropylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-pyran-3-yl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

12
[ 367-93-1 ]
isopropyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

13
[ 367-93-1 ]
isopropyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-3-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

14
[ 367-93-1 ]
diosgenyl 4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

15
[ 367-93-1 ]
Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4aR,6S,7R,8S,8aS)-6-isopropylsulfanyl-2-phenyl-7-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

16
[ 367-93-1 ]
isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

17
[ 367-93-1 ]
isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

18
[ 367-93-1 ]
C₅₁H₇₀O₁₅ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

19
[ 367-93-1 ]
diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

20
[ 367-93-1 ]
diosgenyl 2,3,4-tri-O-acetyl-β-d-xylopyranosyl-(1->2)-3-O-acetyl-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

21
[ 367-93-1 ]
diosgenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

22
[ 367-93-1 ]
diosgenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-benzylidene-β-D-galactopyranoside [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5497 - 5500

23
[ 367-93-1 ]
[ 615570-33-7 ]