(4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 160593-12-4
• Molecular Formula: C₅₇H₆₀O₁₁
• Molecular Weight: 921.097

Synonyms:(4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 5 articles about (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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:

lactose octaacetate (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,52554-32-2) → (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (160593-12-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 30percent HBr/AcOH / CH₂Cl₂

2: HgO, HgBr₂, 3A molecular sieves / toluene; nitromethane / 1 h

3: Na, MeOH

4: 92 percent / zinc chloride / 8 h / Ambient temperature

5: NaH / dimethylformamide

With methanol; 3 A molecular sieve; hydrogen bromide; sodium; sodium hydride; acetic acid; mercury dibromide; mercury(II) oxide; zinc(II) chloride; In nitromethane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(94)00189-8

Reference yield:

allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (50256-34-3,97777-13-4,103136-39-6) → (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (160593-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Na, MeOH

2: 92 percent / zinc chloride / 8 h / Ambient temperature

3: NaH / dimethylformamide

With methanol; sodium; sodium hydride; zinc(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)00189-8

Reference yield:

(2S,3R,4S,5R,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (52211-61-7) → (4aR,6S,7R,8S,8aS)-6-((2R,3R,4S,5R,6R)-6-Allyloxy-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (160593-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / zinc chloride / 8 h / Ambient temperature

2: NaH / dimethylformamide

With sodium hydride; zinc(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)00189-8

upstream raw materials:

benzyl bromide

allyl 4',6'-O-benzylidene-β-lactoside

lactose octaacetate

allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

allyl O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1-4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

C₇₂H₇₉NO₁₆

Allyl O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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