2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester

Base Information

• Chemical Name: 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester
• CAS No.: 215876-09-8
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 215876-09-8.mol

Synonyms:(3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester

Chemical Property of 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester

Chemical Property:

• Boiling Point: 448.8±45.0 °C(Predicted)
• PKA: 14.01±0.20(Predicted)
• Density: 1.122±0.06 g/cm3(Predicted)
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

2,4-Dideoxy-6-O-(phenylmethyl)-L-threo-hexonicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2,4-Dideoxy-6-O-(phenylmethyl)-L-threo-hexonic Acid tert-Butyl Ester is used in the preparation of (3R,5R)-Rosuvastatin (R700510), phorboxazole B and bryostatin 2.

Technology Process of 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester

There total 7 articles about 2,4-Dideoxy-6-O-(phenylMethyl)-L-threo-hexonic Acid tert-Butyl Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate (147849-63-6) → (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (215876-09-8) + (3S,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (549502-23-0)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -35 ℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(19980918)37:17<2354::AID-ANIE2354>3.0.CO;2-9

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) + (Z)-1,3-bis(trimethylsiloxy)-1-tert-butoxybuta-1,3-diene (146431-18-7) → (3R,5S)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (153716-95-1) + (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (215876-09-8) + (3S,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (549502-23-0) + (3S,5S)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester

Guidance literature:

benzyloxyacetoaldehyde; (Z)-1,3-bis(trimethylsiloxy)-1-tert-butoxybuta-1,3-diene; chiral copper(II) complex; In dichloromethane; at -95 ℃;

With pyridinium p-toluenesulfonate; In methanol;

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -25 ℃; Further stages. Title compound not separated from byproducts.;

DOI:10.1002/anie.200603654

Reference yield:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate (147849-63-6) → (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (215876-09-8)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -33 ℃;

DOI:10.1021/ja002356g

upstream raw materials:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate

benzyloxyacetoaldehyde

(Z)-1,3-bis(trimethylsiloxy)-1-tert-butoxybuta-1,3-diene

acetic acid tert-butyl ester

Downstream raw materials:

(4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one

(4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one

(2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol

Refernces

• 1、 Everaere, Kathelyne,Franceschini, Nicolas,Mortreux, André,Carpentier, Jean-Fran?ois. "Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation". . p. 2569 - 2571. Retrieved 2007/10/03.
• 2、 Evans, David A.,Carter, Percy H.,Carreira, Erick M.,Prunet, Joelle A.,Charette, Andre B.,Lautens, Mark. "Asymmetric synthesis of bryostatin 2". . p. 2354 - 2359. Retrieved 2007/10/03.