178231-95-3

Basic information

• Product Name: Calystegine B3
• Synonyms: Calystegine B3;Calystegin B3;2-Epicalystegine B2;(1R,2R,3R,4S,5R)-8-Azabicyclo[3.2.1]octane-1,2,3,4-tetrol;(1R,2S,3R,4R,5R)-8-azabicyclo[3.2.1]octane-2,3,4,5-tetrol
• CAS NO: 178231-95-3
• Molecular Formula: C7H13NO4
• Molecular Weight: 175.18242
• Mol File: 178231-95-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 341.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.722±0.06 g/cm3(Predicted)
• PKA: 13.45±0.70(Predicted)
• CAS DataBase Reference: Calystegine B3(CAS DataBase Reference)
• NIST Chemistry Reference: Calystegine B3(178231-95-3)
• EPA Substance Registry System: Calystegine B3(178231-95-3)

Safety Data

• Hazardous Substances Data: 178231-95-3(Hazardous Substances Data)

Upstream product

• 1236156-22-1 C₄₀H₄₃NO₆ 
• 959409-98-4 (2S,3S,4R,5S)-5-(N-benzyloxycarbonyl)-amino-2,3,4-tris(benzyloxy)-cycloheptanone 
• 1379671-98-3 C₁₅H₂₈O₄Si 
• 1379672-01-1 C₁₀H₁₅NO₆ 
• 1379671-99-4 1-((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-one 
• 1379672-00-0 1-((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-one 
• 1379672-02-2 (3aR,7S,8S,8aS)-8-hydroxy-2,2-dimethyl-7-nitrotetrahydro-3aH-cyclohepta[d][1,3]dioxol-4(5H)-one 
• 1379672-04-4 tert-butyl ((3aS,4S,5S,8aR)-4-hydroxy-2,2-dimethyl-8-oxohexahydro-3aH-cyclohepta[d][1,3]dioxol-5-yl)carbamate 
• 146236-96-6 (2R,3S,4R,5S) 5-azido-2,3,4-tris(benzyloxy) cycloheptane-1-one 
• 332178-31-1 (2S,3R,4S,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone 
• 248582-41-4 (2S,3R,4S,5R)-2,4-dibenzyloxy-5-benzyloxycarbonylamino-3-hydroxycyclohept-6-en-1-one 
• 159639-25-5 (2S,3R,4S,5S) 5-azido-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-one 
• 146176-81-0 (2S,3R,4S,5R)-5-Azido-2,3,4-tris-benzyloxy-cycloheptanone 
• 1310825-99-0 (2S,3S,4S,5R)-5-[(N-benzyl-N-(benzyloxycarbonyl))amino]-2,3,4-tris(benzyloxy)-cycloheptanone 

Relevant articles and documents

Synthesis of nortropane alkaloid calystegine B2 from methyl α-D-xylopyranoside

A new synthetic route for formation of a central cycloheptanone intermediate leading to the nortropane alkaloid calystegine B2 is described. The approach installs the desired ketone functionality directly in a ring-closing metathesis step. The

Method for preparing calystegine and intermediate thereof

The invention relates to the field of the synthesis of natural products, and discloses a method for preparing calystegine and an intermediate thereof. The calystegine has a structure as shown in a formula I. The method comprises the following steps of, in the presence of a protecting agent, carrying out a protective reaction on a hydroxyl group in primary alcohol as shown in a formula II; enabling alkene as shown in a formula III to react with ozone; carrying out an ylide reaction on aldehyde as shown in a formula IV; carrying out a deprotection reaction on alkenyl iodine as shown in a formula V; enabling alcohol as shown in a formula VI to react with a first oxidizing agent; carrying out an NHK (Nozaki-Hiyama-Kishi) reaction on aldehyde as shown in a formula VII; enabling alcohol as shown in a formula VIII to react with a second oxidizing agent; carrying out a reducing reduction on an unsaturated ketone as shown in a formula IX. By using the method, the calystegine is efficiently synthesized with a succinct route through raw materials which are easily obtained and are further low-cost. Through the method, a new route is provided for the synthesis of calystegine-series compounds, and a firm foundation is provided for screening a compound with a biological activity and a medicinal value. The formula I is shown in the description.

First total synthesis of 3-Epi-calystegin B2

A straightforward chiral pool synthesis for a non-natural calystegin, 3-epi-B2, is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs' catalyst-mediated ring closu