(2S,5S,7S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

Base Information

• Chemical Name: (2S,5S,7S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene
• CAS No.: 113643-46-2
• Molecular Formula: C₄₄H₆₂O₈
• Molecular Weight: 718.971

Synonyms:

Chemical Property of (2S,5S,7S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

There total 34 articles about (2S,5S,7S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene 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: 81.0%

(3R,4S)-4-[(2S,9S,10S,12R,15R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-ol (126419-22-5) → (2S,9S,10S,12R,13Z,15R)-2-<(2R,5R,6S)-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-9-<(R)-1-ethyl-2-oxobutyl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (113643-46-2,120330-24-7,120330-25-8)

Guidance literature:

With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1248/cpb.37.1717

Reference yield:

D-Glucose (2280-44-6) → (R)-4-[(2S,5R,7S,9S,10S,12R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one (113643-46-2,120330-24-7,120330-25-8)

Guidance literature:

Multi-step reaction with 9 steps

3: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

4: 96 percent / PPh₃ / benzene / 80 °C

5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

7: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

8: 88 percent / H₂ / Lindlar / methanol

9: 1.) DMSO,(COCl)2, Et₃N, 2.) CSA / 1.) CH₂Cl₂, 2.) CH₂Cl₂, room temperature

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)80703-0

Reference yield:

D-Glucose (2280-44-6) → (R)-4-[(2S,5S,7S,9S,10S,12R)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one (113643-46-2,120330-24-7,120330-25-8)

Guidance literature:

Multi-step reaction with 9 steps

3: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

4: 96 percent / PPh₃ / benzene / 80 °C

5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

7: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

8: 88 percent / H₂ / Lindlar / methanol

9: 1.) DMSO,(COCl)2, Et₃N, 2.) CSA / 1.) CH₂Cl₂, 2.) CH₂Cl₂, room temperature

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)80703-0

upstream raw materials:

(2S,5R,6R,7Z)-2-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-8-<(2R,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

D-Glucose

(2R,3R,6S)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol

(3R,4R,7S)-7-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-4,7-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)oct-1-yne

Downstream raw materials:

C₅₇H₈₄O₁₂

C₅₇H₈₄O₁₂

(R)-4-[(2S,9S,10S,12R,15R)-2-((2R,5R,6S)-5-Ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one

21-epi-20-O-(4-methoxybenzyl)-28-O-benzylsalinomycin

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