{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Base Information

• Chemical Name: {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
• CAS No.: 884902-43-6
• Molecular Formula: C₃₅H₄₂N₂O₁₁S
• Molecular Weight: 698.791

Synonyms:{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Chemical Property of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

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Technology Process of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

There total 3 articles about {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 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: 98.0%

{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-1-[4-(4-formyl-phenoxy)-benzyl]-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester (884902-43-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2006.01.035

Reference yield:

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate (313679-55-9) → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester (884902-43-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / H₂ / Pd/C / tetrahydrofuran

2: 46 percent / Cu(OAc)2; pyridine; 4 Angstroem sieves

3: 98 percent / NaBH₄ / methanol; tetrahydrofuran

With pyridine; sodium tetrahydroborate; copper diacetate; 4 A molecular sieve; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2006.01.035

Reference yield:

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate (313679-57-1) → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-1-[4-(4-hydroxymethyl-phenoxy)-benzyl]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester (884902-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / Cu(OAc)2; pyridine; 4 Angstroem sieves

2: 98 percent / NaBH₄ / methanol; tetrahydrofuran

With pyridine; sodium tetrahydroborate; copper diacetate; 4 A molecular sieve; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2006.01.035

upstream raw materials:

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate

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