(1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol

Base Information

• Chemical Name: (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol
• CAS No.: 192573-98-1
• Molecular Formula: C₄₉H₆₄O₇Si
• Molecular Weight: 793.128
• Mol file: 192573-98-1.mol

Synonyms:(1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol

Chemical Property of (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol

There total 9 articles about (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-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: 76.0%

(Z)-(5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-12-methyl-4-methylene-13-phenyl-tridec-2-en-7-one → (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol (192573-98-1)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4039(97)00885-X

Reference yield:

(2R)-2-methyl-3-phenylpropanal (5445-77-2,63262-79-3,78964-59-7,42307-59-5) → (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol (192573-98-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) B-methoxybis(2-isocaranyl)borane, 2.) H₂O₂ / 1.) Et₂O, -78 deg C, 4 h, 2.) aq. NaOH, reflux, 16 h

2: 2.) Oxone / 1.) AIBN / 1.) PhMe, 90 deg C, 72 h, 2.) MeOH/H₂O, 20 deg C, 4 h

3: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

4: 1.) n-BuLi, 2.) (COCl)2/DMSO, 3.) Et₃N / 1.) THF/Et₂O (5:1), -78 deg C, 1h; -40 deg C, 70 min, 2.) CH₂Cl₂, -78 deg C, 65 min, 3.) to 0 deg C, 40 min

5: 6percent Na(Hg), Na₂HPO₄ / methanol; tetrahydrofuran / 2 h / 20 °C

6: HF/py / pyridine; tetrahydrofuran / 4.5 h / 20 °C

7: 76 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; Oxone; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; B-methoxy-bis(2-isocaranyl)borane; hydrogen fluoride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4039(97)00885-X

Reference yield:

benzyl bromide (100-39-0) → (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol (192573-98-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / LDA, LiCl / tetrahydrofuran / 0.33 h / 0 °C

2: 1.) LiAl(OEt)3H, 2.) HCl / 1.) hexane/THF, -78 deg C to 0 deg C, 1 h, 2.) TFA, 20 deg C, 5 min

3: 1.) B-methoxybis(2-isocaranyl)borane, 2.) H₂O₂ / 1.) Et₂O, -78 deg C, 4 h, 2.) aq. NaOH, reflux, 16 h

4: 2.) Oxone / 1.) AIBN / 1.) PhMe, 90 deg C, 72 h, 2.) MeOH/H₂O, 20 deg C, 4 h

5: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

6: 1.) n-BuLi, 2.) (COCl)2/DMSO, 3.) Et₃N / 1.) THF/Et₂O (5:1), -78 deg C, 1h; -40 deg C, 70 min, 2.) CH₂Cl₂, -78 deg C, 65 min, 3.) to 0 deg C, 40 min

7: 6percent Na(Hg), Na₂HPO₄ / methanol; tetrahydrofuran / 2 h / 20 °C

8: HF/py / pyridine; tetrahydrofuran / 4.5 h / 20 °C

9: 76 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; Oxone; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; B-methoxy-bis(2-isocaranyl)borane; hydrogen fluoride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; lithium triethoxyaluminum hydride; triethylamine; lithium chloride; lithium diisopropyl amide; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4039(97)00885-X

upstream raw materials:

(2R)-2-methyl-3-phenylpropanal

benzyl bromide

(2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol

(2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide

Downstream raw materials:

(1S,3R,4S,5R,6R,7S)-7-Benzyloxy-3,4-bis-benzyloxymethyl-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-5-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,6-diol