(2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

Base Information

• Chemical Name: (2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 400091-05-6
• Molecular Formula: C23H26 O7
• Molecular Weight: 414.45
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID30449882
• Wikidata: Q82269419
• Mol file: 400091-05-6.mol

Synonyms:400091-05-6;(2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol;4-Methoxyphenyl 3-O-allyl-4,6-O-benzylidene-b-D-galactopyranoside;DTXSID30449882;CS-0226027;M1589;A873504;4-Methoxyphenyl 3-O-Allyl-4,6-O-benzylidene-|A-D-galactopyranoside;4-Methoxyphenyl 4,6-O-benzylidene-3-O-prop-2-en-1-yl-beta-D-galactopyranoside

Chemical Property of (2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 228 °C
• Refractive Index: -47.5 ° (C=0.5, Pyridine)
• Boiling Point: 589.86oC at 760 mmHg
• PKA: 12.58±0.70(Predicted)
• Flash Point: 310.536oC
• PSA: 75.61000
• Density: 1.278g/cm3
• LogP: 2.84520
• Storage Temp.: Freezer
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 414.16785316
• Heavy Atom Count: 30
• Complexity: 530

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Methoxyphenyl 3-O-allyl-4,6-O-benzylidene-b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C3C(O2)COC(O3)C4=CC=CC=C4)OCC=C)O
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]3[C@H](O2)CO[C@@H](O3)C4=CC=CC=C4)OCC=C)O

Technology Process of (2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

There total 5 articles about (2S,4aR,6S,7R,8R,8aS)-8-(Allyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-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: 91.0%

benzaldehyde dimethyl acetal (1125-88-8) + p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside (144985-19-3) → 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside (400091-05-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

Reference yield:

4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside (400091-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene / 16 h / Heating

1.2: 74 percent / Bu₄NBr / tetrahydrofuran / 8 h / Heating

2.1: 91 percent / TsOH*H₂O / tetrahydrofuran / 2 h / 25 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside (400091-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol; tetrahydrofuran

2: 1) Bu₂SnO, 2) Bu₄NBr / 1) THF, toluene, 2) THF

3: TsOH*H₂O / tetrahydrofuran

With tetrabutylammomium bromide; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)61200-5

upstream raw materials:

benzaldehyde dimethyl acetal

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside

4-methoxyphenyl β-D-galactopyranoside

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester

Acetic acid (4aR,6S,7R,8S,8aS)-8-allyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

(4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-3-acetoxy-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Goto, Fumitaka,Ogawa, Tomoya. "SYNTHESIS OF A SULFATED GLYCOPEPTIDE CORRESPONDING TO THE CARBOHYDRATE-PROTEIN LINKAGE REGION OF PROTEOGLYCANS: β-D-GlcA-(1->3)4)>-β-D-Gal-(1->3)-β-D-Gal-(1->4)-β-D-Xyl-(1->3)-Ser". . p. 5099 - 5102. Retrieved 2007/10/02.