Methyl2-O-allyl-3-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside

Base Information

• Chemical Name: Methyl2-O-allyl-3-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside
• CAS No.: 210297-54-4
• Molecular Formula: C24H28 O6
• Molecular Weight: 412.48
• Mol file: 210297-54-4.mol

Synonyms:a-D-Mannopyranoside, methyl3-O-(phenylmethyl)-4,6-O-(phenylmethylene)-2-O-2-propenyl- (9CI)

Chemical Property of Methyl2-O-allyl-3-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside

Chemical Property:

• PSA: 55.38000
• LogP: 3.62850

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl2-O-Allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-O-Allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (cas# 210297-54-4) is a compound useful in organic synthesis.

Technology Process of Methyl2-O-allyl-3-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside

There total 1 articles about Methyl2-O-allyl-3-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside 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: 99.0%

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (23392-28-1) + allyl bromide (106-95-6) → methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (210297-54-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 3h;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield: 96.0%

methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (210297-54-4) → methyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside (210297-56-6)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane; for 0.75h; Heating;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield:

methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (210297-54-4) → (2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol (211231-15-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.75 h / Heating

2: (COCl)2, Me₂SO / CH₂Cl₂ / 1 h / -60 °C

3: 32 percent / Mg / tetrahydrofuran / 14 h

4: 87.6 percent / NaH (50percent oil susp.) / dimethylformamide / 8 h

5: 90.9 percent / 1,4-diaminobicyclo<2.2.2>octane / Wilkinson's catalyst / ethanol; benzene; H₂O / 3 h / Heating

With lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; bicyclo[2.2.2] octane-1,4-diamine; sodium hydride; magnesium; dimethyl sulfoxide; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0008-6215(98)00037-8

upstream raw materials:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

allyl bromide

Downstream raw materials:

methyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside

(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol

(2S,3S,4S,5S,6R)-3-Allyloxy-4,5-bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran

3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

Refernces