(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

Base Information

Chemical Name:(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran
CAS No.:382615-99-8
Molecular Formula:C₃₆H₅₅BO₄Si
Molecular Weight:590.727
Hs Code.:

(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

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Chemical Property of (2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

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Technology Process of (2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

There total 15 articles about (2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran 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:

: 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

: 382615-99-8
(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 15 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 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; 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; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 2.1: Sharpless asymmetric epoxidation / 4.1: Wittig methylenation;
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

: 382615-99-8
(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 14 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 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; 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; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Sharpless asymmetric epoxidation / 3.1: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315203-85-1
(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 382615-99-8
(2S,3R,5S,6R)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-6-(9-bora-bicyclo[3.3.1]non-9-ylmethyl)-5-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide; various solvent(s) / 1.67 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 1.75 h / 20 °C

2.2: 95 percent / sodium hydroxide; hydrogen peroxide / H₂O / 20 °C

3.1: 76 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1 h / Heating

4.1: 90 percent / p-toluenesulfonic acid monohydrate / methanol; CH₂Cl₂ / 3 h / 20 °C

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

6.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

7.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

8.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

9.1: tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; camphor-10-sulfonic acid; potassium tert-butylate; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)00164-8