(4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane

Base Information

• Chemical Name: (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane
• CAS No.: 204447-34-7
• Molecular Formula: C₄₃H₆₆O₈
• Molecular Weight: 710.992

Synonyms:(4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane

Chemical Property of (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane

There total 13 articles about (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane 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: 80.0%

[7-(2-Heptyl-[1,3]dioxolan-2-yl)-heptyl]-triphenyl-phosphonium; bromide + (4R,5R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane-5-carbaldehyde → (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane (204447-34-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(97)10754-7

Reference yield:

5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol (146916-76-9) → (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane (204447-34-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Red-Al; 2.) I₂ / 1.) Et₂O, 0 deg C to 25 deg C; 2.) Et₂O, -50 deg C to 25 deg C

2: PPTS / CH₂Cl₂

3: 1.) t-BuLi / 1.) Et₂O, -78 deg C; 2.) DMF

4: DIBAH / CH₂Cl₂ / -78 °C

5: NaH, n-Bu₄NI / tetrahydrofuran / Heating

6: PPTS / methanol / Heating

7: diisopropyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -30 °C

8: CuI / tetrahydrofuran / -25 °C

9: PPTS / benzene / Heating

10: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) THF, H₂O; 2.) THF, H₂O

11: 80 percent / n-BuLi / tetrahydrofuran / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; L-(+)-diisopropyl tartrate; 4 A molecular sieve; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(97)10754-7

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (4R,5R)-5-[(Z)-8-(2-Heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-4-[2-(4-methoxy-benzyloxy)-ethyl]-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxane (204447-34-7)

Guidance literature:

Multi-step reaction with 13 steps

1: NaH, n-Bu₄NI / tetrahydrofuran

2: n-BuLi / tetrahydrofuran

3: 1.) Red-Al; 2.) I₂ / 1.) Et₂O, 0 deg C to 25 deg C; 2.) Et₂O, -50 deg C to 25 deg C

4: PPTS / CH₂Cl₂

5: 1.) t-BuLi / 1.) Et₂O, -78 deg C; 2.) DMF

6: DIBAH / CH₂Cl₂ / -78 °C

7: NaH, n-Bu₄NI / tetrahydrofuran / Heating

8: PPTS / methanol / Heating

9: diisopropyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / -30 °C

10: CuI / tetrahydrofuran / -25 °C

11: PPTS / benzene / Heating

12: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) THF, H₂O; 2.) THF, H₂O

13: 80 percent / n-BuLi / tetrahydrofuran / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; L-(+)-diisopropyl tartrate; 4 A molecular sieve; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(97)10754-7

upstream raw materials:

5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

p-methoxybenzyl chloride

1-but-3-ynyloxymethyl-4-methoxy-benzene

(Z)-3-Iodo-5-(4-methoxy-benzyloxy)-pent-2-en-1-ol

Downstream raw materials:

{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-[(Z)-8-(2-heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-methanol

(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-[(Z)-8-(2-heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxane-4-carboxylic acid methyl ester

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