(2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol

Base Information

• Chemical Name: (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol
• CAS No.: 246530-90-5
• Molecular Formula: C₂₁H₂₉NO₉
• Molecular Weight: 439.463
• Mol file: 246530-90-5.mol

Synonyms:(2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol

Chemical Property of (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol

There total 4 articles about (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol 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:

(S)-2-Benzyloxycarbonylamino-3-[(3S,3aR,6R,6aR)-6-(3-diethylboranyl-propoxy)-hexahydro-furo[3,2-b]furan-3-yloxy]-propionic acid methyl ester → (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol (246530-90-5)

Guidance literature:

With dihydrogen peroxide; sodium acetate; In tetrahydrofuran; water; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00599-2

Reference yield:

Isosorbide (652-67-5) → (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol (246530-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 15 percent / K₂CO₃ / toluene / 24 h / Heating

2: 25 percent / BF₃*Et₂O / CHCl₃ / 0 - 20 °C

3: tetrahydrofuran / 5.5 h / -10 - 20 °C

4: 291 mg / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 - 20 °C

With boron trifluoride diethyl etherate; dihydrogen peroxide; sodium acetate; potassium carbonate; In tetrahydrofuran; chloroform; water; toluene; 1: Alkylation / 2: Addition / 3: Addition / 4: Oxidation;

DOI:10.1016/S0040-4020(99)00599-2

Reference yield:

6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol (103617-76-1) → (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol (246530-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 25 percent / BF₃*Et₂O / CHCl₃ / 0 - 20 °C

2: tetrahydrofuran / 5.5 h / -10 - 20 °C

3: 291 mg / NaOAc; H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 - 20 °C

With boron trifluoride diethyl etherate; dihydrogen peroxide; sodium acetate; In tetrahydrofuran; chloroform; water; 1: Addition / 2: Addition / 3: Oxidation;

DOI:10.1016/S0040-4020(99)00599-2

upstream raw materials:

Isosorbide

6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol

(2'S)-5-O-allyl-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-1,4:3,6-dianhydro-D-sorbitol