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Merck
CN

265004

(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol

97%

Synonym(s):

(−)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol, (−)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4R,5R)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane, 1,1,4,4-Tetraphenyl-2,3-O-isopropylidene-L-threitol, TADDOL

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About This Item

Empirical Formula (Hill Notation):
C31H30O4
CAS Number:
93379-48-7
Molecular Weight:
466.57
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24856048
MDL number:
MFCD00064467
Beilstein/REAXYS Number:
3657855

Key Documents

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Product Name

(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol, 97%

InChI

1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1

SMILES string

CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccccc2)c3ccccc3)C(O)(c4ccccc4)c5ccccc5

InChI key

OWVIRVJQDVCGQX-VSGBNLITSA-N

assay

97%

optical activity

[α]19/D −62.6°, c = 1 in chloroform

mp

193-195 °C (lit.)

functional group

ether
hydroxyl
ketal
phenyl

Quality Level

100

Related Categories

Application

Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding

Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides

Reactant or reagent involved in:
  • Enantioswitching of catalytic asymmetric hydroboration
  • Synthesis of derivative ligands for asymmetric hydroformylation of alkenes
  • Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes
  • Addition of deactivated alkyl Grignard reagents to aldehydes

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB0317
MKCT4028
MKCS0226
MKCS6495
MKCN1585

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Jung-Shen B Tai et al.
Physical review. E, 101(4-1), 042702-042702 (2020-05-20)
Chiral condensed matter systems, such as liquid crystals and magnets, exhibit a host of spatially localized topological structures that emerge from the medium's tendency to twist and its competition with confinement and field coupling effects. We show that the strength
Jung-Shen B Tai et al.
Science (New York, N.Y.), 365(6460), 1449-1453 (2019-10-12)
Starting with Gauss and Kelvin, knots in fields were postulated to behave like particles, but experimentally they were found only as transient features or required complex boundary conditions to exist and could not self-assemble into three-dimensional crystals. We introduce energetically

Articles

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

Chiral Diols

TADDOLs demonstrate versatility in metal-catalyzed asymmetric reactions and as Brønsted acid organocatalysts in hetero-Diels–Alder reactions.

(-)-反-α,α'-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯甲醇)

由Seebach小组开发的手性助剂TADDOL（α,α,α,α-四芳基-1,3-二氧戊环-4,5-二甲醇）在不对称合成中具有多种应用，包括从用作化学计量手性试剂或用于路易斯酸介导的反应，到在催化加氢和立体规则复分解聚合中发挥作用。

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