217438-72-7

Basic information

• Product Name: Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester
• CAS NO: 217438-72-7
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.27346
• Product Categories: N-BOC
• Mol File: 217438-72-7.mol

Chemical Properties

• Boiling Point: 342.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• PKA: 11.98±0.40(Predicted)
• CAS DataBase Reference: Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester(217438-72-7)
• EPA Substance Registry System: Carbamic acid, [(1R,4S)-4-hydroxy-2-cyclohexen-1-yl]-, 1,1-dimethylethyl ester(217438-72-7)

Safety Data

• Hazardous Substances Data: 217438-72-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 266306-65-4 tert-butyl (1S,4R)-2-oxa-3-aza-bicyclo-[2,2,2]oct-5-ene-3-carboxylate 
• 77300-23-3 cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate 
• 740798-68-9 acetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester 
• 266306-44-9 (1S,4R)-3-aza-2-oxabicyclo<2,2,2>oct-5-ene hydrochloride 
• 1165952-91-9 cyclohexa-1,3-diene 

Downstream Products

• 455330-42-4 4R-(4-oxocyclohex-2-enyl)carbamic acid tert-butyl ester 
• 1620561-13-8 (1R,2R,3S,4S,5S)-5-benzamido-2,3,4-trihydroxycyclohexanaminium 2,2,2-trifluoroacetate 
• 1620555-88-5 C₁₁H₂₁NO₅ 
• 1620555-85-2 (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate 
• 1620555-86-3 tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate 

Relevant articles and documents

Asymmetric stereodivergent strategy towards aminocyclitols

A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2-deoxystreptamine analogues and conduramine A, is described. The Pd-catalyzed asymmetric desymmetrization of meso 1,4-dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α-glucosidase inhibitors.

α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights

α-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a β-oxygenated moiety led to a domino [4+2] cycloaddition/σN-O bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the σN-O bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported.

α-Chloronitroso compounds derived from carbohydrate ketones: Cycloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine

1,2-O-Isopropylidene-α-D-xylofuranose 9 was converted into 5-O-(tert-butyldiphenylsilyl)-3-chloro-3-deoxy-1,2-O-isopropylidene-3-C-nitroso- α-o-xylofuranose 17 in four steps, and a similar α-chloronitroso compound 8 was synthesised from 1,2:5,6-di-O-isopropylidene-α-o-glucofuranose 6, the structures of 8 and 17 being confirmed by X-ray crystallography. Reaction of 8 or 17 with cyclohexa-1,3-diene in the presence of small amounts of water gave the cycloadduct (1S,4R)-3-aza-2-oxabicyclo[2.2.2]oct-5-ene, as its hydrochloride (-)-2, in ≥96% ee. Reactions of either 8 or 17 with cyclohepta-1,3-diene similarly gave (1R,5S)-7-aza-6-oxabicyclo[3.2.2]non-8-ene hydrochloride (-)-25 with ≥96% ee, but reactions with cyclopentadiene proceeded differently, with 17 giving the nitrone (E)-(3 R,5 R)-3-[5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-1′,2′-O-is opropylidene-α-D-erythro-pentofuranos-3′-ylidene-amino]-5-chlorocycl opentene N-oxide 19, the structure of which was determined by X-ray crystallography. The dihydrooxazines (-)-25 and (-)-2 were used in syntheses of (-)-physoperuvine (-)-34 and (+)-epibatidine (+)-40, respectively. A pseudoenantiomeric α-chloronitroso compound 51 was also prepared from 2,3-O-isopropylidene-α-L-sorbofuranose 44, and reaction of 51 with cyclohexa-1,3-diene gave (+)-2 with 97% ee.

Asymmetric cycloadditions of dienes to chloronitroso compounds derived from carbohydrate ketones: Syntheses of (-)-physoperuvine and (+)-epibatidine

An α-chloronitroso compound derived from D-xylose undergoes cycloadditions with cyclic dienes to give bicyclic dihydrooxazines of high enantiomeric purity; such adducts were used in a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidin