Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 212199-00-3
• Molecular Formula: C₂₈H₃₄ClNO₉
• Molecular Weight: 564.032
• Mol file: 212199-00-3.mol

Synonyms:Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester

There total 1 articles about Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-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: 78.0%

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) + ethyl 2-O-acetyl-4-O-benzyl-3-O-monochloroacetyl-1-thio-α-L-rhamnopyranoside → Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester (212199-00-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane;

DOI:10.1016/S0008-6215(97)10013-1

Reference yield: 69.0%

Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester (212199-00-3) → Acetic acid (2R,3R,4R,5R,6S)-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (212199-01-4)

Guidance literature:

With 2,6-dimethylpyridine; hydrazine dithiocarbonate; acetic acid; In dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(97)10013-1

Reference yield:

Chloro-acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-methyl-tetrahydro-pyran-4-yl ester (212199-00-3) → 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / AcOH, 2,6-lutidine, hydrazine dithiocarbonate / CH₂Cl₂; ethyl acetate

2: 34 percent / mol. sieves 4A, MeOTf / CH₂Cl₂; diethyl ether / 4 h / 0 °C

3: 1) DABCO, RhCl(PPh₃)3, 2) HgO, HgCl₂ / 1) EtOH, toluene, H₂O, reflux, 3 h, 2) acetone, H₂O, 1 h

4: 52 percent / mol. sieves 4A, TMSOTf / diethyl ether / 1 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; RhCl(PPh₃)3; hydrazine dithiocarbonate; 4 A molecular sieve; acetic acid; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(97)10013-1

upstream raw materials:

3-[(N-benzyloxycarbonyl)amino]propanol

Downstream raw materials:

Acetic acid (2R,3R,4R,5R,6S)-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

3-N-benzyloxycarbonylaminopropyl (3-O-allyl-2,4-6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

C₆₅H₇₇NO₂₁