5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene

Base Information

• Chemical Name: 5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene
• CAS No.: 129264-66-0
• Molecular Formula: C₇₇H₈₂O₁₀Si
• Molecular Weight: 1195.58
• Mol file: 129264-66-0.mol

Synonyms:

Chemical Property of 5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene

There total 1 articles about 5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene 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: 68.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate (129264-65-9,144539-19-5) + 1,1-dibromomethane (74-95-3) → 5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene (129264-66-0)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; In tetrahydrofuran;

DOI:10.1021/jo00305a008

Reference yield:

5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene (129264-66-0) → (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-2-ol

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00305a008

Reference yield:

5(R)-(tert-butyldiphenylsilyloxy)-3(S),4(S),6-tribenzyloxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-1-hexene (129264-66-0) → (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hex-5-en-2-ol + 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-β-D-fructofuranoside (129264-67-1)

Guidance literature:

With potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; Mechanism; Product distribution; multistep reaction, excellent diastereoselectivity;

DOI:10.1016/0008-6215(92)80059-A

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate

1,1-dibromomethane

Downstream raw materials:

3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-β-D-fructofuranoside