methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside
• CAS No.: 383862-63-3
• Molecular Formula: C₄₁H₅₂O₁₀
• Molecular Weight: 704.858
• Mol file: 383862-63-3.mol

Synonyms:methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside

There total 1 articles about methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside 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: 80.0%

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) + methyl 2,3,4-tri-O-benzyl-6,7,8-trideoxy-8-tributylstannyl-oct-6-eno-α-D-manno-1,5-pyranoside → methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-talo-D-glycero-undecoside + methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-galacto-D-glycero-undecoside + methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside (383862-63-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(01)00331-7

Reference yield:

allyl bromide (106-95-6) + methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside (383862-63-3) → (4R,5R,4'R)-5-[(1S,2R)-1-Allyloxy-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-enyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(01)00331-7

Reference yield:

methyl 2,3,4-tri-O-benzyl-6-deoxy-8,9:10,11-di-O-isopropylidene-6-vinyl-α-D-manno-D-gulo-D-glycero-undecoside (383862-63-3) → (S)-2-((2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-enal

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / dimethylformamide; various solvent(s) / 2 h / 20 °C

2.1: H₂SO₄ / tetrahydrofuran; H₂O / 16 h / Heating

2.2: sodium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: sodium borohydride / tetrahydrofuran; methanol / 3 h

4.1: sodium periodate / diethyl ether; H₂O / 0.5 h / 20 °C

With sodium tetrahydroborate; sodium periodate; sulfuric acid; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(01)00331-7

upstream raw materials:

2,2:4,5-di-O-isopropylidene-D-arabinose

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-vinyl-α-D-manno-D-glycero-heptoside

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-vinyl-α-D-manno-D-erythro-octoside