[(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 315204-00-3
• Molecular Formula: C₂₈H₄₁IO₄Si
• Molecular Weight: 596.621

Synonyms:[(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

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Technology Process of [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

There total 14 articles about [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-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: 95.0%

[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol (315203-87-3) → [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (315204-00-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 20 ℃;

DOI:10.1016/S0040-4039(00)01483-0

Reference yield:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-enoic acid methyl ester (213815-23-7) → [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (315204-00-3)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; camphor-10-sulfonic acid; 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:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-but-2-en-1-ol (315204-07-0) → [(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-iodomethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (315204-00-3)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; camphor-10-sulfonic acid; 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

upstream raw materials:

[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

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

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

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

[(3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-methylene-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

(4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene

Acetic acid (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

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