(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

Base Information

Chemical Name:(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol
CAS No.:929202-63-1
Molecular Formula:C₂₀H₂₄O₅
Molecular Weight:344.408
Hs Code.:

Synonyms:(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

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Chemical Property of (R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

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Technology Process of (R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

There total 3 articles about (R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol 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: 75.0%

: 903900-29-8
(E)-(4R,5R)-4,5,6-Tris-benzyloxy-hex-2-en-1-ol

: 929202-63-1
(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

Guidance literature:: (E)-(4R,5R)-4,5,6-Tris-benzyloxy-hex-2-en-1-ol; With titanium(IV) isopropylate; 4 A molecular sieve; D-(-)-diisopropyl tartrate; In dichloromethane; at -25 ℃; for 0.5h;

With tert.-butylhydroperoxide; In dichloromethane; at -25 - 0 ℃; for 24h;
DOI:10.1016/j.tetasy.2006.04.022

Reference yield: 52.0%

: 903900-29-8
(E)-(4R,5R)-4,5,6-Tris-benzyloxy-hex-2-en-1-ol

: 67-64-1
acetone

: 929202-63-1
(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

: (2R,3R,4S,5R)-1,2-O-isopropylidene-3,6-anhydro-4,5-di-O-benzyl-D-galactitol

Guidance literature:: (E)-(4R,5R)-4,5,6-Tris-benzyloxy-hex-2-en-1-ol; With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; 4 A molecular sieve; In dichloromethane; at -25 - 0 ℃; for 14h;

acetone; With citric acid; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tetasy.2006.12.010

Reference yield:

: (E)-(4R,5R)-4,5,6-Tris-benzyloxy-hex-2-enal

: 929202-63-1
(R)-1-((2R,3S,4R)-3,4-Bis-benzyloxy-tetrahydro-furan-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaBH₄; CeCl₃*7H₂O / ethanol / 20 °C

2.1: Ti(O-i-Pr)4; D-(-)-DIPT; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -25 °C

2.2: 75 percent / t-BuOOH / CH₂Cl₂ / 24 h / -25 - 0 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; D-(-)-diisopropyl tartrate; In ethanol; dichloromethane; 2.2: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2006.04.022