142436-07-5

Basic information

• Product Name: 2,3,4,5-O-Tetrabenzyl-D-myo-inositol
• Synonyms: 2,3,4,5-O-Tetrabenzyl-D-myo-inositol
• CAS NO: 142436-07-5
• Molecular Weight: 540.656
• Mol File: 142436-07-5.mol

Chemical Properties

• CAS DataBase Reference: 2,3,4,5-O-Tetrabenzyl-D-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-O-Tetrabenzyl-D-myo-inositol(142436-07-5)
• EPA Substance Registry System: 2,3,4,5-O-Tetrabenzyl-D-myo-inositol(142436-07-5)

Safety Data

• Hazardous Substances Data: 142436-07-5(Hazardous Substances Data)

Upstream product

• 129662-34-6 (+/-)-1,2,4/3-2,3-Di-O-(2-methoxyethoxymethyl)cyclohex-5-ene-1,2,3,4-tetrol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 131146-88-8 (±)-4-O-allyl-1-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 131146-96-8 (+/-)-1,2,6-tri-O-allyl-3-O-benzyl-4,5-O-isopropylidene-myo-inositol 
• 116786-69-7 (+/-)-1,6-di-O-allyl-4,5-di-O-benzyl-myo-inositol 
• 131147-02-9 (+/-)-1,6-di-O-allyl-3,4,5-tri-O-benzyl-myo-inositol 
• 131147-11-0 (±)-2,3-O-isopropylidene-1,5,6-tri-O-benzyl-4-O-allyl-myo-inositol 
• 131147-00-7 (3aS,4R,5R,6S,7R,7aR)-6,7-Bis-allyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5-diol 
• 100-39-0 benzyl bromide 
• 6404-82-6 (+/-)-1,2-O-isopropylidene-myo-inositol 
• 115072-69-0 (+/-)-1,6-di-O-allyl-2,3:4,5-di-O-isopropylidene-myo-inositol 
• 115072-70-3 (+/-)-1,6-di-O-allyl-myo-inositol 
• 38643-30-0 (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 114342-82-4 5,6-di-O-benzyl-3,4-bis-O-(4-methoxybenzyl)-myo-inositol 

Downstream Products

• 131233-74-4 2-O,3-O,4-O,5-O-tetrabenzyl-L-myo-inositol 
• 132437-54-8 1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 110550-27-1 (1S,2R,3R,4S)-cyclohex-5-ene-1,2,3,4-tetrayltetrakis(oxy)tetrakis(methylene)tetrabenzene 
• 6195-45-5 (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol 
• 260392-75-4 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 
• 150772-66-0 (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 260447-16-3 1-D-6-O-allyl-2,3,4,5-tetra-O-benzyl-myo-inositol 
• 129261-63-8 (+)-1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol 
• 131146-82-2 C₅₄H₆₀O₁₂ 
• 131146-82-2 C₅₄H₆₀O₁₂ 

Relevant articles and documents

Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation

O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.

Achievement of ring inversion of myo-inositol derivatives due to silyloxy/silyloxy repulsion enhanced by the trans-substituents on both sides

The introduction of quite bulky trialkyl or diarylalkylsilyl groups into vicinal trans-hydroxy groups induced a conformational flip of certain multifunctionalized cyclohexane rings from the usual chair form possessing more equatorial substituents (equatorial-rich chair form) into another chair-form that has more axial substituents (axial-rich chair form). This realization was experimentally revealed by the conformational study of the synthetic myo-inositol derivatives possessing two tert-butyldimethylsilyl (TBS), two triisopropylsilyl (TIPS), or two tert-butyldiphenylsilyl (TBDPS) groups on an adjacent trans-diol. Among them, the cyclohexane rings of the 4,5-bis-O-TIPS-myo-inositol, 4,5-bis-O-TBDPS-myo-inositol, and 1,2,3,6-tetra-O-benzyl-4,5-bis-O-TBDPS-myo-inositol were in the axial-rich chair form. Comparison of the ring conformations also revealed that the order of the repulsion was OTBDPS/OTBDPS>OTIPS/OTIPS>OTBS/OTBS, and the silyloxy/silyloxy repulsion was enhanced when the two silyloxy groups were placed in the center of the contiguous four equatorial substituents.

Stable axial-rich chair conformer of myo-inositol derivatives due to introduction of two adjacent bulky silyl protections

The ring-conformational change of myo-inositol derivatives by introducing two tert-butyldimethylsilyl, triisopropylsilyl, or tert-butyldiphenylsilyl groups into the 1,2-trans hydroxy groups - 3,4- and 4,5-positions - were investigated. The cyclohexane cores of the 4,5-bis-O-silylated derivatives with tert-butyldiphenylsilyl or triisopropylsilyl groups were present in the axial-rich chair form.

1,2-Diacetals in synthesis: Total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei

A full account on a total synthesis of GPI anchor 1 employing butanediacetal (BDA) groups and a chiral bis(dihydropyran) is presented. The reactivity of selenium and thio glycosides was tuned by the use of BDA groups. This allowed the assembly of an appro

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction

Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.

Dispiroketals in Synthesis (Part 19): Dispiroketals as Enantioselective and Regioselective Protective Agents for Symmetric Cyclic and Acyclic Polyols.

The enantioselective preparation of both enantiomers of a C2-symmetric diphenyl-bidihydropyran 3 and 4 is described.The application of enantiopure bi-dihydropyrans 1-4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated.Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

Dispiroketals in Synthesis (Part 11): Concomitant Enantioselective and Regioselective Protection of 2,5-Dibenzoyl-myo-inositol.

2,5-Dibenzoyl-myo-inositol, a symmetrical polyol, may be simultaneously enantioselectively and regioselectively protected using the chiral dienes (1), (2) and (3).Deprotection, to afford D or L-1,6-tetra-O-benzyl-myo-inositol (8) and (12) respectively, wa

Parasite Glucoconjugates. Part 1. The Synthesis of Some Early and Related Intermediates in the Biosynthetic Pathway of Glycosyl-phosphatidylinositol Membrane Anchors

The enantio-pure 1D- and 1L-myo-inositol derivative 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respective