(2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol

Base Information

• Chemical Name: (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol
• CAS No.: 236427-87-5
• Molecular Formula: C₃₉H₅₄O₁₀
• Molecular Weight: 682.852

Synonyms:

Chemical Property of (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol

There total 24 articles about (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol 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:

(2R,5S,6S,8S,10S)-10-(2-Benzyloxy-ethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol → (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol (236427-87-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: 81 percent / H₂ / Raney Ni (W₂) / ethanol / 4 h / Ambient temperature

3: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / Ambient temperature

4: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1.5 h

5: Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

6: SmI₂ / tetrahydrofuran; methanol / 1 h / -95 - -80 °C

7: Zn-Cu couple, NH₄Cl / methanol / 0.17 h / Ambient temperature

8: 60 percent / HF, H₂O / acetonitrile; tetrahydrofuran / 11 h / Ambient temperature

With 2,6-dimethylpyridine; n-butyllithium; samarium diiodide; hydrogen fluoride; water; hydrogen; copper; ammonium chloride; Dess-Martin periodane; zinc; Raney Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1055/s-1999-2689

Reference yield:

{(2R,5S,6S,8S,10S)-10-(2-Benzyloxy-ethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-triethyl-silane (236427-81-9) → (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol (236427-87-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / H₂ / Raney Ni (W₂) / ethanol / 4 h / Ambient temperature

2: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / Ambient temperature

3: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1.5 h

4: Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

5: SmI₂ / tetrahydrofuran; methanol / 1 h / -95 - -80 °C

6: Zn-Cu couple, NH₄Cl / methanol / 0.17 h / Ambient temperature

7: 60 percent / HF, H₂O / acetonitrile; tetrahydrofuran / 11 h / Ambient temperature

With n-butyllithium; samarium diiodide; hydrogen fluoride; water; hydrogen; copper; ammonium chloride; Dess-Martin periodane; zinc; Raney Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1055/s-1999-2689

Reference yield:

4-benzyloxy-2-butyn-1-ol (91142-50-6) → (2R,5S,6S,8R,10S)-10-((1S,2S,3S,5S,7R)-7-Benzyloxymethyl-2-hydroxy-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecan-5-ol (236427-87-5)

Guidance literature:

Multi-step reaction with 20 steps

1: 73 percent / LAH / tetrahydrofuran / 7.5 h / -78 - 0 °C

2: 93 percent / L-(+)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

3: 94 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 2 h / Ambient temperature

4: 94 percent / NaOH, H₂O / methanol / 0.75 h / Ambient temperature

5: 76 percent / pyridine / CH₂Cl₂ / 18 h / 0 °C

6: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / 0 °C

7: 98 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 48 h

9: benzene / 21 h / Ambient temperature

10: 99 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

11: 93 percent / D-(-)-DET, TBHP, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -25 °C

12: 96 percent / diethyl ether / 23 h / -30 °C

13: 76 percent / Bu₃P / CH₂Cl₂ / 4 h / Ambient temperature

14: 100 percent / (i-Pr)2NEt, TBAI / 1,2-dichloro-ethane / 6 h / Heating

15: 95 percent / m-CPBA, NaH₂PO₄ / CH₂Cl₂ / 0.42 h / Ambient temperature

16: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1.5 h

17: Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

18: SmI₂ / tetrahydrofuran; methanol / 1 h / -95 - -80 °C

19: Zn-Cu couple, NH₄Cl / methanol / 0.17 h / Ambient temperature

20: 60 percent / HF, H₂O / acetonitrile; tetrahydrofuran / 11 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; tributylphosphine; 4 A molecular sieve; hydrogen fluoride; water; tetra-(n-butyl)ammonium iodide; copper; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetonitrile; benzene;

DOI:10.1055/s-1999-2689

upstream raw materials:

4-benzyloxy-2-butyn-1-ol

benzyl bromide

{(2R,3S)-3-[(1S,2R)-3-Benzyloxy-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-oxiranyl}-methanol

(2S,3S,4S,5R)-6-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hexane-1,3-diol

Downstream raw materials:

10-[7-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-6,8-dioxa-bicyclo[3.2.1]oct-5-ylmethyl]-5-(tert-butyl-dimethyl-silanyloxy)-2-[2-(4-methoxy-benzyloxy)-ethyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane

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