(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

Base Information

Chemical Name:(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
CAS No.:365441-18-5
Molecular Formula:C₇₂H₉₆O₉Si₂
Molecular Weight:1161.72
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 17 articles about (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 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: 77.0%

: 365441-09-4
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide

: 365441-10-7
{3-bromo-1-[2-(4-methoxy-benzyloxy)-1-methyl-6-trityloxy-hexyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane

: 365441-18-5
(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

Guidance literature:: With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 0.416667h;
DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 365441-18-5
(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

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

9: 77 percent / t-BuLi / diethyl ether / 0.42 h / -78 °C

With 2,6-dimethylpyridine; lead(IV) acetate; tin; osmium(VIII) oxide; n-butyllithium; 4 A molecular sieve; potassium tert-butylate; tert.-butyl lithium; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 3: Brown crotylboration;
DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

: 76-83-5
trityl chloride

: 365441-18-5
(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

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

9: 77 percent / t-BuLi / diethyl ether / 0.42 h / -78 °C

With 2,6-dimethylpyridine; lead(IV) acetate; tin; osmium(VIII) oxide; n-butyllithium; 4 A molecular sieve; potassium tert-butylate; tert.-butyl lithium; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 3: Brown crotylboration;
DOI:10.1016/S0040-4039(01)01069-3