((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane

Base Information

• Chemical Name: ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane
• CAS No.: 853260-31-8
• Molecular Formula: C₃₁H₃₆O₄Si
• Molecular Weight: 500.71

Synonyms:((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane

Chemical Property of ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane

Chemical Property:

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Technology Process of ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane

There total 3 articles about ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-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: 60.0%

(3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-trimethylsilanylethynyl-tetrahydro-furan-2-ol (863871-31-2) → ((2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane + ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane (853260-31-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1016/j.tetlet.2005.03.017

Reference yield:

tri-O-benzyl-D-arabinolactone (14233-64-8) → ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane (853260-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / N-BuLi / tetrahydrofuran / -78 °C

2: 60 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -78 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.03.017

Reference yield:

trimethylsilylacetylene (1066-54-2) → ((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-ylethynyl)-trimethyl-silane (853260-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / N-BuLi / tetrahydrofuran / -78 °C

2: 60 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -78 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.03.017

upstream raw materials:

(3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-trimethylsilanylethynyl-tetrahydro-furan-2-ol

tri-O-benzyl-D-arabinolactone

trimethylsilylacetylene

Downstream raw materials:

C₅₄H₅₄O₈

3,6-anhydro-4,5,7-tri-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-D-manno-heptitol

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