(1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Base Information

• Chemical Name: (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol
• CAS No.: 161596-04-9
• Molecular Formula: C₂₈H₃₀O₄
• Molecular Weight: 430.544
• Mol file: 161596-04-9.mol

Synonyms:(1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Chemical Property of (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

There total 29 articles about (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol 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: 95.0%

(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (151693-64-0) → (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-04-9)

Guidance literature:

With sodium methylate; In methanol; for 15h; Ambient temperature;

DOI:10.1039/P19940002017

Reference yield:

(4R,5R,6S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enone (163563-91-5) → (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-04-9) + (1S,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-05-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; ethanol; at -78 ℃; for 0.166667h; Title compound not separated from byproducts.;

DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

C20H26O6 (942041-32-9) → (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol (161596-04-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

2.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

3.1: BH₃*Me₃S; NaOH; H₂O₂ / tetrahydrofuran / 24 h

3.2: oxalyl chloride; DMSO / CH₂Cl₂ / 4 h / -78 °C

4.1: 94 percent / Et₃N / CH₂Cl₂ / 168 h / 20 °C

5.1: 92 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.17 h / 0 °C

6.1: 78 percent / NaH / dimethylformamide / 1 h / 20 °C

7.1: 66 percent / Cu(OTf)2; BH₃*THF / 1 h

8.1: 86 percent / PPh₃; I₂; imidazole / toluene / 3 h / Heating

9.1: 60 percent / DBU / tetrahydrofuran / Heating

10.1: 93 percent / HgCl₂ / acetone; H₂O / 1 h / Heating

11.1: 53 percent / MsCl; DAMP / pyridine / 24 h / 20 °C

12.1: NaBH₄; CeCl₃*7H₂O / ethanol; tetrahydrofuran / 0.17 h / -78 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; borane-THF; bisacodyl; water; dihydrogen peroxide; iodine; copper(II) bis(trifluoromethanesulfonate); sodium hydride; acetic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; mercury dichloride; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 10.1: Ferrier rearrangement;

DOI:10.1016/j.tetlet.2007.03.031

upstream raw materials:

(1R,2R,3R,4R)-1-O-acetyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

(1R,2R,3R,4S,6R)-1,2-di-O-benzyl-6-benzyloxymethyl-4-phenylselenocyclohexane-1,2,3-triol

(4R,5R,6S)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohex-2-enone

C₂₂H₂₄O₆

Downstream raw materials:

(1R,2S,3S,4S,5R,6R)-3-O-acetyl-4,5-di-O-benzyl-6-benzyloxymethyl-1,2-epoxycyclohexane-3,4,5-triol

(1S,2R,3S,4S,5R,6R)-3-O-acetyl-4,5-di-O-benzyl-6-benzyloxymethyl-1,2-epoxycyclohexane-3,4,5-triol

(1S,2R,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol

(1R,2S,3R,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-ol