(1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

Base Information

• Chemical Name: (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one
• CAS No.: 674336-07-3
• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.547

Synonyms:(1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

Chemical Property of (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one

There total 16 articles about (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-9-one 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: 63.0%

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester (674335-93-4) → (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one (674336-07-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/ja037957x

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one (674336-07-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 93 percent / TfOH / diethyl ether / 4 h / 20 °C

2.1: 95 percent / HCl / methanol / 0.17 h / 20 °C

3.1: 93 percent / PCC / CH₂Cl₂ / 4 h

4.1: LHMDS / tetrahydrofuran / -78 - 25 °C

4.2: tetrahydrofuran / 18 h / -78 - 25 °C

5.1: 1.19 g / Hg(OAc)2; aq. KI / tetrahydrofuran; H₂O / 0.5 h

6.1: 75 percent / diethyl ether / 4 h / -78 °C

7.1: 95 percent / aq. LiOH*H₂O / methanol; tetrahydrofuran / 6 h / Heating

8.1: 80 percent / Et₃N / acetone / 48 h / 52 °C

9.1: 90 percent / Bu₄NI; aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

10.1: 63 percent / NaH / tetrahydrofuran / 4 h / Heating

With hydrogenchloride; lithium hydroxide; sodium hydroxide; trifluorormethanesulfonic acid; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; pyridinium chlorochromate; potassium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/ja037957x

Reference yield:

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid (674336-06-2) → (1S,11S,13R,15R)-11-Allyl-15-benzyloxy-7-methoxymethoxy-10,17-dioxa-tricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one (674336-07-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Et₃N / acetone / 48 h / 52 °C

2: 90 percent / Bu₄NI; aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

3: 63 percent / NaH / tetrahydrofuran / 4 h / Heating

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja037957x

upstream raw materials:

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

O-benzyl 2,2,2-trichloroacetimidate

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid cyanomethyl ester

Downstream raw materials:

((1S,11R,13R,15R)-15-Benzyloxy-7-methoxymethoxy-9-oxo-10,17-dioxa-tricyclo[11.3.1.0^3,8]heptadeca-3⁽⁸⁾,4,6-trien-11-yl)-acetaldehyde

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