3-Cyclohexene-1,2,5,6-tetrol, 3-(hydroxymethyl)-1-methyl-4-[1,4,5-tris(methoxymethoxy)-2-naphthalen yl]-, 2,5,6-triacetate, (1R,2R,5S,6R)-

Base Information

• Chemical Name: 3-Cyclohexene-1,2,5,6-tetrol, 3-(hydroxymethyl)-1-methyl-4-[1,4,5-tris(methoxymethoxy)-2-naphthalen yl]-, 2,5,6-triacetate, (1R,2R,5S,6R)-
• CAS No.: 917113-33-8
• Molecular Formula: C30H38O14
• Molecular Weight: 622.623
• Mol file: 917113-33-8.mol

Synonyms:

Chemical Property of 3-Cyclohexene-1,2,5,6-tetrol, 3-(hydroxymethyl)-1-methyl-4-[1,4,5-tris(methoxymethoxy)-2-naphthalen yl]-, 2,5,6-triacetate, (1R,2R,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclohexene-1,2,5,6-tetrol, 3-(hydroxymethyl)-1-methyl-4-[1,4,5-tris(methoxymethoxy)-2-naphthalen yl]-, 2,5,6-triacetate, (1R,2R,5S,6R)-

There total 8 articles about 3-Cyclohexene-1,2,5,6-tetrol, 3-(hydroxymethyl)-1-methyl-4-[1,4,5-tris(methoxymethoxy)-2-naphthalen yl]-, 2,5,6-triacetate, (1R,2R,5S,6R)- 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:

C36H52O14Si → C30H38O14 (917113-33-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at 20 ℃; for 12h;

DOI:10.1021/ja066621v

Reference yield:

C17H27BrO6Si (917113-23-6) → C30H38O14 (917113-33-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 24 h / 0 °C

2.1: 85 percent / 2,4,6-collidine / CH₂Cl₂ / 8 h / 5 °C

3.1: 95 percent / Super-Hydride / 1,2-dichloro-ethane; tetrahydrofuran / 0.5 h / 60 °C

4.1: 90 percent / K-10 clay / CH₂Cl₂ / 4 h / 20 °C

5.1: 70 percent / AsPh₃; CuCl; DIEA / Pd₂(dba)3 / acetonitrile / 4 h / 70 °C

6.1: 80 percent / Super-Hydride / tetrahydrofuran / 1 h / -78 °C

7.1: Ti(iPrO)4 / CH₂Cl₂ / 0.5 h / 20 °C

7.2: 60 percent / CH₂Cl₂ / 10 h / 20 °C

8.1: 140 mg / pyridine / 2 h / 20 °C

9.1: 78 mg / Et₃N-3HF / acetonitrile / 12 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; titanium(IV) isopropylate; triphenyl-arsane; K-10 clay; lithium triethylborohydride; acetic acid; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; copper(l) chloride; tetramethylammonium triacetoxyborohydride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 5.1: Stille cross-coupling;

DOI:10.1021/ja066621v

Reference yield:

C18H31BrO8SiS (917113-28-1) → C30H38O14 (917113-33-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / Super-Hydride / 1,2-dichloro-ethane; tetrahydrofuran / 0.5 h / 60 °C

2.1: 90 percent / K-10 clay / CH₂Cl₂ / 4 h / 20 °C

3.1: 70 percent / AsPh₃; CuCl; DIEA / Pd₂(dba)3 / acetonitrile / 4 h / 70 °C

4.1: 80 percent / Super-Hydride / tetrahydrofuran / 1 h / -78 °C

5.1: Ti(iPrO)4 / CH₂Cl₂ / 0.5 h / 20 °C

5.2: 60 percent / CH₂Cl₂ / 10 h / 20 °C

6.1: 140 mg / pyridine / 2 h / 20 °C

7.1: 78 mg / Et₃N-3HF / acetonitrile / 12 h / 20 °C

With pyridine; titanium(IV) isopropylate; triphenyl-arsane; K-10 clay; lithium triethylborohydride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; copper(l) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 3.1: Stille cross-coupling;

DOI:10.1021/ja066621v

upstream raw materials:

C₁₇H₂₇BrO₆Si

C₁₈H₃₁BrO₈SiS

C₁₇H₂₉BrO₅Si

C₁₄H₂₃BrO₄Si

Downstream raw materials:

C₃₀H₃₆O₁₅

C₂₆H₂₆O₁₂

Refernces