(E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

Base Information

• Chemical Name: (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol
• CAS No.: 220172-58-7
• Molecular Formula: C₄₀H₅₀O₁₀
• Molecular Weight: 690.831
• Mol file: 220172-58-7.mol

Synonyms:(E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

Chemical Property of (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

There total 5 articles about (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-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: 95.0%

(E)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone (220172-57-6) → (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol (220172-58-7)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1039/a807190j

Reference yield:

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) → (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol (220172-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / benzene / Ambient temperature

2: 95 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

With zinc(II) tetrahydroborate; In diethyl ether; benzene;

DOI:10.1039/a807190j

Reference yield:

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate (55610-71-4) → (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol (220172-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

2: 90 percent / 18-crown-6, K₂CO₃ / toluene / 16 h / Ambient temperature

3: 95 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

With n-butyllithium; zinc(II) tetrahydroborate; 18-crown-6 ether; potassium carbonate; In diethyl ether; toluene;

DOI:10.1039/a807190j

upstream raw materials:

(E)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosiduronyl)-(triphenylphosphoranylidene)methane

dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate

Downstream raw materials:

(1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol

(2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-((1R,2R,3S,4S,5R,6R)-1,2,3,4,5,6,7-heptakis-benzyloxy-heptyl)-6-methoxy-tetrahydro-pyran

methyl 2,3,4,6,7,8-hexa-O-benzyl-9,10:11,12-di-O-isopropylidene-α-L-erythro-L-manno-D-gluco-1,5-pyranoside

(2R,3R,4S,5S,6R,7R)-5,6,7-Tris-benzyloxy-7-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-heptane-1,2,3,4-tetraol