{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane
CAS No.:346584-04-1
Molecular Formula:C₅₀H₆₆O₉Si
Molecular Weight:839.154
Hs Code.:

{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

Synonyms:{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

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Chemical Property of {(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

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Technology Process of {(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

There total 18 articles about {(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane 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: 88.0%

: 824-94-2
p-methoxybenzyl chloride

: 346584-03-0
(2R,4aR,6S,7R,9aS)-6-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 346584-04-1
{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 213815-23-7
(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester

: 346584-04-1
{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 18 steps

1.1: 7.34 g / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

2.1: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

3.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

4.1: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

5.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

6.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3.5 h / 20 °C

7.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

8.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

8.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

9.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

10.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

11.1: imidazole / dimethylformamide / 9 h / 50 °C

12.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

13.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

14.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

15.1: tetrahydrofuran / 3 h / 20 °C

16.1: NaHCO₃; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / tetrahydrofuran; H₂O; dimethylformamide / 24 h / 20 °C

16.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

17.1: BH₃*THF / tetrahydrofuran / -30 °C

17.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

18.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane-THF; pyridine-SO₃ complex; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; (-)-diethyl tartrate; triethylamine; triphenylphosphine; dimeric 9-borabicyclo[3.3.1]nonane; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 2.1: Sharpless asymmetric epoxidation / 4.1: Wittig methylenation / 16.1: Suzuki coupling;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315204-07-0
(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-en-1-ol

: 346584-04-1
{(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 17 steps

1.1: 87 percent / (-)-diethyl tartrate; titanium(IV) isopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 - 20 °C

2.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

3.1: 5.38 g / tetrahydrofuran / 0.5 h / 0 °C

4.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

5.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3.5 h / 20 °C

6.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

7.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

7.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

8.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

9.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

10.1: imidazole / dimethylformamide / 9 h / 50 °C

11.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

12.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

13.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

14.1: tetrahydrofuran / 3 h / 20 °C

15.1: NaHCO₃; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / tetrahydrofuran; H₂O; dimethylformamide / 24 h / 20 °C

15.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

16.1: BH₃*THF / tetrahydrofuran / -30 °C

16.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

17.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; borane-THF; pyridine-SO₃ complex; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; (-)-diethyl tartrate; triethylamine; triphenylphosphine; dimeric 9-borabicyclo[3.3.1]nonane; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Sharpless asymmetric epoxidation / 3.1: Wittig methylenation / 15.1: Suzuki coupling;
DOI:10.1016/S0040-4020(01)00164-8