C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate)

Base Information

• Chemical Name: C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate)
• CAS No.: 1201913-68-9
• Molecular Formula: C₃₀H₃₄O₁₄
• Molecular Weight: 618.592
• DSSTox Substance ID: DTXSID601098484
• Mol file: 1201913-68-9.mol

Synonyms:SCHEMBL15354334;DTXSID601098484;C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate)

Chemical Property of C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate)

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 16
• Exact Mass: 618.19485575
• Heavy Atom Count: 44
• Complexity: 996

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=CC=C(C=C1)CC2=CC3=C(COC34C(C(C(C(O4)COC(=O)OC)OC(=O)OC)OC(=O)OC)OC(=O)OC)C=C2
• Isomeric SMILES: CCC1=CC=C(C=C1)CC2=CC3=C(CO[C@@]34[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)OC)OC(=O)OC)OC(=O)OC)OC(=O)OC)C=C2

Technology Process of C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate)

There total 10 articles about C,C',C''-[(1S,3'R,4'S,5'R,6'R)-6-[(4-Ethylphenyl)methyl]-3',4',5',6'-tetrahydro-6'-[[(methoxycarbonyl)oxy]methyl]spiro[isobenzofuran-1(3H),2'-[2H]pyran]-3',4',5'-triyl] tris(C-methyl carbonate) 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: 92.0%

(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) + methyl chloroformate (79-22-1) → (1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] (1201913-68-9)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 20.1667h; Inert atmosphere;

DOI:10.1021/acs.joc.5b02734

Reference yield: 88.0%

(1S,3′R,4′R,5′S,6′R)-6-[(methoxycarbonyloxy)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] + 4-ethylphenylboronic acid (63139-21-9) → (1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] (1201913-68-9)

Guidance literature:

(1S,3′R,4′R,5′S,6′R)-6-[(methoxycarbonyloxy)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran]; 4-ethylphenylboronic acid; With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; In 1,2-dimethoxyethane; Inert atmosphere;

With N-acetylcystein; ethyl acetate; In 1,2-dimethoxyethane; for 1h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere; Cooling;

DOI:10.1021/acs.joc.5b02734

Reference yield:

2-bromo-1,4-benzenedicarboxylic acid (586-35-6) → (1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] (1201913-68-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: borane-THF / tetrahydrofuran / 7 h / 0 - 35 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere

3.1: n-butyllithium / toluene; hexane / 1.08 h / 5 °C / Inert atmosphere

3.2: 2.5 h / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

5.1: dmap / dichloromethane / 4.67 h / -10 - 20 °C / Inert atmosphere

6.1: potassium carbonate; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / 1,2-dimethoxyethane / Inert atmosphere

6.2: 1 h / Inert atmosphere; Cooling

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; borane-THF; palladium diacetate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 6.1: |Suzuki Coupling;

DOI:10.1021/acs.joc.5b02734

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

methyl chloroformate

D-Glucono-1,5-lactone

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

(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)

(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