(1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate)

Base Information

• Chemical Name: (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate)
• CAS No.: 1201913-74-7
• Molecular Formula: C₄₂H₅₈O₁₀
• Molecular Weight: 722.917
• Mol file: 1201913-74-7.mol

Synonyms:(1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate)

Chemical Property of (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate)

There total 10 articles about (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) 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: 68.0%

(1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzoyl)-6'-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) → (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) (1201913-74-7)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In 1,2-dimethoxyethane; isopropyl alcohol; at 20 ℃; for 7h; Inert atmosphere;

DOI:10.1021/acs.oprd.8b00400

Reference yield:

(1S,3′R,4′S,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol (903565-83-3) + pivaloyl chloride (3282-30-2) → (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) (1201913-74-7)

Guidance literature:

dmap; In dichloromethane; at 20 ℃; for 24h; Cooling with ice;

Reference yield:

2,3,4,5-tetrakis(trimethylsiloxy)-6-trimethylsilyloxymethyl-2-(5-(4-ethylphenyl)hydroxymethyl-2-(1-methoxy-1-methylethoxymethyl)phenyl)tetrahydropyran (1201913-63-4) → (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) (1201913-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / acetonitrile; water / 5.5 h / 20 °C / Inert atmosphere

2: hydrogen / 5% Pd(II)/C(eggshell) / 1,2-dimethoxyethane / 4 h / 20 °C

3: dmap / dichloromethane / 24 h / 20 °C / Cooling with ice

With hydrogenchloride; hydrogen; dmap; 5% Pd(II)/C(eggshell); In 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;

upstream raw materials:

(1S,3′R,4′S,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol

pivaloyl chloride

2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene

(2,4-dibromophenyl)methanol

Downstream raw materials:

(1S,3′R,4′S,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol