.beta.-D-Allopyranoside, (3aS,4R,5R,6R,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(phenylmethoxy)methyl-4H-cyclopentoxazol-4-yl 2-deoxy-4-O-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(R)-phenylmethylene-.beta.

Base Information

• Chemical Name: .beta.-D-Allopyranoside, (3aS,4R,5R,6R,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(phenylmethoxy)methyl-4H-cyclopentoxazol-4-yl 2-deoxy-4-O-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(R)-phenylmethylene-.beta.
• CAS No.: 144448-35-1
• Molecular Formula: C₇₂H₇₀N₄O₁₆
• Molecular Weight: 1247.36

Synonyms:b-D-Allopyranoside,2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-[(phenylmethoxy)methyl]-4H-cyclopentoxazol-4-yl2-deoxy-4-O-[2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(phenylmethylene)-b-D-allopyranosyl]-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-,[3aS-[3aa,4a(S*),5b,6a,6aa]]-; 4H-Cyclopentoxazole, b-D-allopyranoside deriv.; Pyrano[3,2-d]-1,3-dioxin, b-D-allopyranoside deriv.

Chemical Property of .beta.-D-Allopyranoside, (3aS,4R,5R,6R,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(phenylmethoxy)methyl-4H-cyclopentoxazol-4-yl 2-deoxy-4-O-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(R)-phenylmethylene-.beta.

Chemical Property:

• PSA: 212.12000
• LogP: 7.24190

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of .beta.-D-Allopyranoside, (3aS,4R,5R,6R,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(phenylmethoxy)methyl-4H-cyclopentoxazol-4-yl 2-deoxy-4-O-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(R)-phenylmethylene-.beta.

There total 3 articles about .beta.-D-Allopyranoside, (3aS,4R,5R,6R,6aS)-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(phenylmethoxy)methyl-4H-cyclopentoxazol-4-yl 2-deoxy-4-O-2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(R)-phenylmethylene-.beta. 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: 27.0%

(+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8) + 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranosyl trichloroacetimidate → (3aR,4S,5S,6S,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-4H-cyclopentoxazol-4-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (144448-35-1) + 1,5-Anhydro-3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-D-ribo-hex-1-enitol (144448-34-0) + (3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (136773-87-0) + (3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (136845-48-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.333333h; Further byproducts given;

DOI:10.1002/hlca.19920750506

Reference yield:

3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (136773-85-8) → (3aR,4S,5S,6S,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-4H-cyclopentoxazol-4-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (144448-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / K₂CO₃ / CH₂Cl₂ / 16 h / Ambient temperature

2: trimethylsilyl triflate, 4-Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium carbonate; In dichloromethane;

DOI:10.1002/hlca.19920750506

Reference yield:

C59H54N2O13 → (3aR,4S,5S,6S,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-4H-cyclopentoxazol-4-yl 3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (144448-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: water, HgO, HgCl₂ / acetone / 1 h / Ambient temperature

2: 90 percent / K₂CO₃ / CH₂Cl₂ / 16 h / Ambient temperature

3: trimethylsilyl triflate, 4-Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; potassium carbonate; mercury dichloride; mercury(II) oxide; In dichloromethane; acetone;

DOI:10.1002/hlca.19920750506

upstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole

3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

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