methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides

Base Information

• Chemical Name: methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides
• CAS No.: 359765-34-7
• Molecular Formula: C₂₁H₃₀O₇
• Molecular Weight: 394.465
• Mol file: 359765-34-7.mol

Synonyms:methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides

Chemical Property of methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides

There total 1 articles about methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides 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: 71.0%

methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside (132032-75-8) + allyl chloromethyl ether (3970-20-5) → methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides (359765-34-7)

Guidance literature:

With magnesium; In tetrahydrofuran; at -30 ℃;

DOI:10.1016/S0008-6215(01)00103-3

Reference yield: 47.3%

benzyl bromide (100-39-0) + methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides (359765-34-7) → methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranosides + methyl 7-O-allyl-4,6-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside + methyl 7-O-allyl-4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside (359765-35-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -10 ℃;

DOI:10.1016/S0008-6215(01)00103-3

Reference yield:

methyl 7-O-allyl-4-O-benzyl-2,3-O-isopropylidene-L-glycero and D-glycero-α-D-manno-heptopyranosides (359765-34-7) → (S)-Benzyloxy-((3aS,4S,6S,7R,7aS)-7-benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetaldehyde (359765-39-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / -10 °C

2.1: 1,4-diazabicyclo[2.2.2]octane / Wilkinson's catalyst / ethanol; benzene; H₂O / 4 h / Heating

2.2: 80.4 percent / HgCl₂; HgO / acetone; H₂O / 1 h

3.1: Swern reagent

With 1,4-diaza-bicyclo[2.2.2]octane; swern reagent; sodium hydride; Wilkinson's catalyst; In ethanol; water; N,N-dimethyl-formamide; benzene; 3.1: Swern oxidation;

DOI:10.1016/S0008-6215(01)00103-3

upstream raw materials:

methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

allyl chloromethyl ether

Downstream raw materials:

methyl 7-O-allyl-4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside

(S)-Benzyloxy-((3aS,4S,6S,7R,7aS)-7-benzyloxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-acetaldehyde

methyl 4,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptopyranoside