(2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol

Base Information

• Chemical Name: (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol
• CAS No.: 82707-10-6
• Molecular Formula: C₄₆H₆₀O₇
• Molecular Weight: 724.978
• Mol file: 82707-10-6.mol

Synonyms:(2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol

Chemical Property of (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol

There total 27 articles about (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol 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:

(2S,3S,4R,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one (82707-09-3) → (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol (82707-10-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h;

DOI:10.1021/ja00386a076

Reference yield:

benzyl bromide (100-39-0) → (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol (82707-10-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) 20percent Pd(OH)2/C₂H₂, 2.) KH / 1.) dioxane, 2.) THF

2: 76 percent / n-Bu₄NF / tetrahydrofuran

3: 86 percent / COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

4: 87.5 percent / toluene

5: H₂ / Rh/Al₂O₃ / toluene

6: 1.) 25percent AcOH, 2.) NaBH₄ / 1.) 50 deg C, 1 h, 2.) EtOH

7: 92 percent / pyridine / 20 h / 65 °C

8: pyridinium chlorochromate, 4-Angstroem sieves / CH₂Cl₂

9: 76 percent / LDA / tetrahydrofuran / 0.17 h / -70 °C

10: Dibal / toluene / 2 h / -78 °C

With pyridine; palladium dihydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; acetylene; lithium diisopropyl amide; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00386a076

Reference yield:

(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol (82707-03-7) → (2S,3S,6S,7S,8S,9S)-8-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-3,5,7,9-tetramethyl-10-trityloxy-decane-4,6-diol (82707-10-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) 20percent Pd(OH)2/C₂H₂, 2.) KH / 1.) dioxane, 2.) THF

2: 76 percent / n-Bu₄NF / tetrahydrofuran

3: 86 percent / COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

4: 87.5 percent / toluene

5: H₂ / Rh/Al₂O₃ / toluene

6: 1.) 25percent AcOH, 2.) NaBH₄ / 1.) 50 deg C, 1 h, 2.) EtOH

7: 92 percent / pyridine / 20 h / 65 °C

8: pyridinium chlorochromate, 4-Angstroem sieves / CH₂Cl₂

9: 76 percent / LDA / tetrahydrofuran / 0.17 h / -70 °C

10: Dibal / toluene / 2 h / -78 °C

With pyridine; palladium dihydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; acetylene; lithium diisopropyl amide; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00386a076

upstream raw materials:

(2S,3S,4R,6R,7S,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one

(2S,3S,4R,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one

benzyl bromide

(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol