6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole

Base Information

• Chemical Name: 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole
• CAS No.: 906098-22-4
• Molecular Formula: C₂₀H₂₈O₉
• Molecular Weight: 412.437
• Mol file: 906098-22-4.mol

Synonyms:6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole

Chemical Property of 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole

There total 9 articles about 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole 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: 97.1%

6-((3S,4R,5R,6S)-4,5,6-tris(methoxymethoxy)octa-1,7-dien-3-yl)-4-methoxybenzo[d][1,3]dioxole (906098-21-3) → 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole (906098-22-4)

Guidance literature:

With dimethyl sulfoxide; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1021/jo0607562

Reference yield:

(2S,3R,4S)-2,3,4-Tris-methoxymethoxy-hex-5-enal → 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole (906098-22-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1.48 g / CH₂Cl₂ / 10 h / -78 - 20 °C

2.1: Mg / tetrahydrofuran / Heating

2.2: CuI / tetrahydrofuran / 0.5 h / -20 °C

2.3: 76 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

3.1: 90.2 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

4.1: Bu₃P / tetrahydrofuran / 20 °C

5.1: 0.066 g / aq. H₂O₂ / tetrahydrofuran / 20 °C

6.1: 97.1 percent / DMSO / (Cy₃P)2(PhCH=)RuCl₂ / CH₂Cl₂

With lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; magnesium; dimethyl sulfoxide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Wittig olefination;

DOI:10.1021/jo0607562

Reference yield:

(2R,3R,4S)-2,3,4-tri(methoxymethoxy)-5-hexen-1-ol (906098-13-3) → 6-((1S,4S,5R,6S)-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl)-4-methoxybenzo[d][1,3]dioxole (906098-22-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: 1.48 g / CH₂Cl₂ / 10 h / -78 - 20 °C

3.1: Mg / tetrahydrofuran / Heating

3.2: CuI / tetrahydrofuran / 0.5 h / -20 °C

3.3: 76 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

4.1: 90.2 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: Bu₃P / tetrahydrofuran / 20 °C

6.1: 0.066 g / aq. H₂O₂ / tetrahydrofuran / 20 °C

7.1: 97.1 percent / DMSO / (Cy₃P)2(PhCH=)RuCl₂ / CH₂Cl₂

With lithium aluminium tetrahydride; oxalyl dichloride; tributylphosphine; dihydrogen peroxide; magnesium; dimethyl sulfoxide; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.1: Wittig olefination;

DOI:10.1021/jo0607562

upstream raw materials:

6-((3S,4R,5R,6S)-4,5,6-tris(methoxymethoxy)octa-1,7-dien-3-yl)-4-methoxybenzo[d][1,3]dioxole

(2R,3R,4S)-2,3,4-tri(methoxymethoxy)-5-hexen-1-ol

methyl (2E,4R,5R,6S)-4,5,6-tris(methoxymethoxy)-2,7-octadienoate

benzyl 2,3,4-tri-O-methoxymethyl-D-xylopyranoside

Downstream raw materials:

(1R,2R,3S,6R)-6-(4-methoxybenzo[d][1,3]dioxol-6-yl)-4-cyclohexene-1,2,3-triol