1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

Base Information

Chemical Name:1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one
CAS No.:909544-77-0
Molecular Formula:C₅₀H₇₁ClO₈Si₂
Molecular Weight:891.733
Hs Code.:

1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

Synonyms:1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

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Chemical Property of 1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

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Technology Process of 1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

There total 15 articles about 1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-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: 100.0%

: 909544-84-9
1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-ol

: 909544-77-0
1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1016/j.tetlet.2006.06.032

Reference yield:

: 909544-80-5
(2R,3R,4S)-4-Chloro-2-hydroxymethyl-tetrahydro-pyran-3-ol

: 909544-77-0
1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: camphorsulfonic acid / methanol / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

4.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

5.1: 100 percent / K₂CO₃ / methanol

6.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

6.2: 81 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

7.1: 100 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 7.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.06.032

Reference yield:

: 909544-94-1
(2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 909544-77-0
1-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-6-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-hex-4-yn-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / camphorsulfonic acid / methanol

2.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

3.1: camphorsulfonic acid / methanol / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

5.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

6.1: 100 percent / K₂CO₃ / methanol

7.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

7.2: 81 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

8.1: 100 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 8.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.06.032