134877-42-2

Basic information

• Product Name: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate
• Synonyms: T8;((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((Methylsulfonyl)oxy)tetrahydrofuran-2-yl)Methyl benzoate;((2R,3R,5S)-3-(benzoyloxy)-4,4-difluoro-5-((Methylsulfonyl)oxy)tetrahydrofuran-2-yl)Methyl benzoate;2-Deoxy-2,2-difluoro-alpha-D-erythro-pentofuranose 3,5-dibenzoate 1-Methanesulfonate;((2R,3R,5S)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzo;-3-(Benzoyloxy);-4,4-difluoro-5-((methylsulfonyl);((2R,3R,5S)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl be
• CAS NO: 134877-42-2
• Molecular Formula: C₂₀H₁₈F₂O₈S
• Molecular Weight: 456.4139264
• EINECS: 1308068-626-2
• Product Categories: Antineoplastic drug, difluorine nucleoside analog
• Mol File: 134877-42-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 588.439 °C at 760 mmHg
• Flash Point: 309.677 °C
• Appearance: /
• Density: 1.46
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate(134877-42-2)
• EPA Substance Registry System: 2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate(134877-42-2)

Safety Data

• Hazardous Substances Data: 134877-42-2(Hazardous Substances Data)

Usage

Uses

2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose is an impurity of Gemcitabine (G305028), a potential anticancer agent.

InChI:InChI=1/C22H24O8S/c1-22(2)18(29-20(24)16-12-8-5-9-13-16)17(28-21(22)30-31(3,25)26)14-27-19(23)15-10-6-4-7-11-15/h4-13,17-18,21H,14H2,1-3H3/t17-,18-,21-/m1/s1

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 1173824-58-2 (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate 
• 143157-25-9 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-α-ribofuranose 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 
• 153012-08-9 C₁₉H₁₆F₂O₆ 
• 95058-77-8 2-deoxy-2,2-difluoro-1-carbonylribose 
• 928797-50-6 ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate 
• 122111-01-7 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate 

Downstream Products

• 1006598-32-8 1-(3',5'-di-O-benzoyl-2',2'-difluoro-α-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 1006598-31-7 1-(3',5'-di-O-benzoyl-2',2'-difluoro-β-D-pentofuranos-1'-yl)-5-(E)-bromovinyluracil 
• 1321580-95-3 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil 
• 1321580-93-1 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil 
• 1321580-94-2 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil 
• 908337-67-7 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine 
• 122111-03-9 gemcitabine hydrochloride 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 95058-81-4 gemcitabine 

Relevant articles and documents

Method for recovering mother liquor of gemcitabine intermediate

The invention provides a method for recovering mother liquor of a gemcitabine intermediate, and relates to the technical field of purification. The method for recovering the mother liquor of the gemcitabine intermediate provided by the invention comprises the following steps of: performing acidolysis of crystallization mother liquor containing a compound 5 and a compound 10 so as to obtain a mixture of a compound 3 and a compound 9; mixing the mixture of the compound 3 and the compound 9 with aniline, and performing dehydration reaction to obtain a mixture of Schiff base 12 and the compound 9; performing separation of the mixture of the Schiff base 12 and the compound 9 to obtain high-purity Schiff base 12; performing hydrolysis of the high-purity Schiff base 12 to obtain the compound 3; and mixing the compound 3 with methylsulfonyl chloride, and performing acylation reaction so as to obtain the high-purity compound 5. The method provided by the invention can remove the compound 10 in the crystallization mother liquor to obtain the high-purity compound 5, so that the yield and the purity of hydrochloride, namely gemcitabine hydrochloride, are improved.

High-selectivity synthesis method for gemcitabine intermediate

The invention discloses a high-selectivity synthesis method for a gemcitabine intermediate. The high-selectivity synthesis method specifically comprises the following process: Step 1, synthesis of T1;Step2, synthesis of T2, to be specific, 550kg of hydrogen peroxide is dropwise added into the T1, and a reaction is controlled to produce the T2; Step3, synthesis of T3, to be specific, sodium acetate trihydrate or sodium carbonate is added into a reaction kettle, the PH value is adjusted with glacial acetic acid, a 10%-15% sodium hypochlorite aqueous solution is dropwise added, and a reaction iscontrolled to produce the T3; Step 4, synthesis of T4; Step 5, synthesis of T5; Step 6, synthesis of T6; Step 7, synthesis of T7; Step 8, synthesis of T8; and Step9, T8 configuration transformation.The high-selectivity synthetic method for the gemcitabine intermediate can reduce the production cost, and meanwhile, can also increase the yield of the gemcitabine intermediate.

Industrial preparation process for key intermediate sulfonated saccharide of Gemcitabine

The invention relates to a preparation method for a compound represented by a formula (I) shown in the description, i.e., a key intermediate sulfonated saccharide of Gemcitabine. The final product is prepared through subjecting a compound represented by a formula (II) shown in the description to sodium borohydride reduction, hydroxyl protection and resolution. The method is simple in process, high in yield and high in product purity and has no need of harsh reaction conditions, thereby being very suitable for industrial production.