(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol
CAS No.:909544-97-4
Molecular Formula:C₃₈H₄₃ClO₇
Molecular Weight:647.208
Hs Code.:

Synonyms:(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

There total 16 articles about (2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol 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: 94.0%

: 1-((2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-6-((2R,3R,4S)-4-chloro-3-hydroxy-tetrahydro-pyran-2-yl)-hex-4-yn-3-one

: 909544-97-4
(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃;
DOI:10.1016/j.tetlet.2006.06.032

Reference yield:

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

: 909544-97-4
(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 9 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

8.1: 79 percent / HF / acetonitrile / 0 °C

9.1: 94 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0 °C

With 2,6-dimethylpyridine; triethylsilane; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetonitrile; 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

: 909544-97-4
(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 10 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

9.1: 79 percent / HF / acetonitrile / 0 °C

10.1: 94 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0 °C

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