(1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol

Base Information

• Chemical Name: (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol
• CAS No.: 365441-19-6
• Molecular Formula: C₇₂H₉₈O₉Si₂
• Molecular Weight: 1163.74
• Mol file: 365441-19-6.mol

Synonyms:(1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol

Chemical Property of (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol

There total 18 articles about (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-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: 71.0%

(4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-one (365441-18-5) → (1S,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol + (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol (365441-19-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

1 ,5-pentanediol (111-29-5) → (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol (365441-19-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: PCC; molecular sieves 4 Angstroem powder / CH₂Cl₂ / 1.5 h / 20 °C

3: n-BuLi; t-BuOK; (-)-Ipc₂BOMe / BF₃*OEt₂ / tetrahydrofuran / -78 °C

4: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

5: 94 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

6: 96 percent / Pb(OAc)4 / benzene / 0.5 h / 20 °C

7: 64 percent / Sn / tetrahydrofuran; ethanol; H₂O / 4 h / 20 °C / sonication

8: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; lead(IV) acetate; tin; osmium(VIII) oxide; n-butyllithium; 4 A molecular sieve; potassium tert-butylate; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 3: Brown crotylboration;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

trityl chloride (76-83-5) → (1R,4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-ol (365441-19-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: PCC; molecular sieves 4 Angstroem powder / CH₂Cl₂ / 1.5 h / 20 °C

3: n-BuLi; t-BuOK; (-)-Ipc₂BOMe / BF₃*OEt₂ / tetrahydrofuran / -78 °C

4: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

5: 94 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

6: 96 percent / Pb(OAc)4 / benzene / 0.5 h / 20 °C

7: 64 percent / Sn / tetrahydrofuran; ethanol; H₂O / 4 h / 20 °C / sonication

8: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; lead(IV) acetate; tin; osmium(VIII) oxide; n-butyllithium; 4 A molecular sieve; potassium tert-butylate; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 3: Brown crotylboration;

DOI:10.1016/S0040-4039(01)01069-3

upstream raw materials:

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

{3-bromo-1-[2-(4-methoxy-benzyloxy)-1-methyl-6-trityloxy-hexyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane

(4S,5S,6R)-1-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decan-1-one

1 ,5-pentanediol

Downstream raw materials:

(1R,4S,5R,6R)-1-((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-6-(4-methoxy-benzyloxy)-5-methyl-2-methylene-10-trityloxy-decane-1,4-diol

2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-8-trityloxy-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester