(1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane

Base Information

• Chemical Name: (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane
• CAS No.: 181586-77-6
• Molecular Formula: C₂₈H₃₂O₈
• Molecular Weight: 496.557

Synonyms:(1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane

Chemical Property of (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane

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Technology Process of (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane

There total 8 articles about (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.0^5,10]hexadecane 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: 67.0%

(E)-3-Phenyl-acrylic acid (2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-[(E)-(3-phenyl-acryloyl)oxymethyl]-[1,4]dioxan-2-ylmethyl ester (181586-75-4) → (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.05,10]hexadecane (181586-77-6)

Guidance literature:

In toluene; at -60 ℃; for 60h; Irradiation;

DOI:10.1021/jo960556y

Reference yield:

3,3-dimethoxy-butan-2-one (21983-72-2) → (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.05,10]hexadecane (181586-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid / 4 h / 70 °C / 70 Torr

2: 95 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 96 percent / DMAP / CH₂Cl₂; pyridine / 20 h / Ambient temperature

4: toluene / 60 h / -28 °C / Irradiation

With dmap; lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; dichloromethane; toluene;

DOI:10.1021/jo960556y

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → (1R,5S,7R,8R,10S,14R,15S,16S)-7,8-dimethoxy-7,8-dimethyl-2,13-dioxo-15,16-diphenyl-3,6,9,12-tetraoxatricyclo[12.2.0.05,10]hexadecane (181586-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / DMAP / CH₂Cl₂; pyridine / 20 h / Ambient temperature

2: toluene / 60 h / -28 °C / Irradiation

With dmap; In pyridine; dichloromethane; toluene;

DOI:10.1021/jo960556y

upstream raw materials:

(E)-3-Phenyl-acrylic acid (2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-[(E)-(3-phenyl-acryloyl)oxymethyl]-[1,4]dioxan-2-ylmethyl ester

3,3-dimethoxy-butan-2-one

Cinnamoyl chloride

(2S,3S,5R,6R)-2,3-bis(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl<1,4>dioxane

Downstream raw materials:

(1S,2S,3R,4R)-1,2-diphenyl-3,4-bis([(tolyl-4-sulfonyl)oxy]methyl)cyclobutane

(2S,3S,5R,6R)-2,3-bis(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl<1,4>dioxane

((1R,2R,3S,4S)-2-Hydroxymethyl-3,4-diphenyl-cyclobutyl)-methanol

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