Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 175876-88-7
• Molecular Formula: C₆₇H₇₃NO₁₃
• Molecular Weight: 1100.32

Synonyms:Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester

There total 6 articles about Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-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:

5-<(benzyloxycarbonyl)amino>pentanol (87905-98-4) → Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester (175876-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / 4A molecular sieves, silver silicate / CH₂Cl₂; toluene / 17 h / Ambient temperature

2: 88 percent / NaOMe, MeOH / 168 h / Ambient temperature

3: 1.) 3A molecular sieves, 2.) TMSOTf / 1.) CH₂Cl₂, Et₂O, 1.5 h, 2.) CH₂Cl₂, Et₂O, 1,5 h

With methanol; trimethylsilyl trifluoromethanesulfonate; silver silicate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; In dichloromethane; toluene;

DOI:10.1016/0040-4020(95)01093-9

Reference yield:

ethyl 2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside (127753-99-5) → Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester (175876-88-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / pyridine / 2 h

2: Br₂ / CH₂Cl₂ / 0.17 h

3: 59 percent / 4A molecular sieves, silver silicate / CH₂Cl₂; toluene / 17 h / Ambient temperature

4: 88 percent / NaOMe, MeOH / 168 h / Ambient temperature

5: 1.) 3A molecular sieves, 2.) TMSOTf / 1.) CH₂Cl₂, Et₂O, 1.5 h, 2.) CH₂Cl₂, Et₂O, 1,5 h

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; silver silicate; 3 A molecular sieve; 4 A molecular sieve; bromine; sodium methylate; In dichloromethane; toluene;

DOI:10.1016/0040-4020(95)01093-9

Reference yield:

Benzoic acid (2S,3S,4R,5R)-4,5-bis-benzyloxy-6-bromo-2-methyl-tetrahydro-pyran-3-yl ester → Benzoic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester (175876-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / 4A molecular sieves, silver silicate / CH₂Cl₂; toluene / 17 h / Ambient temperature

2: 88 percent / NaOMe, MeOH / 168 h / Ambient temperature

3: 1.) 3A molecular sieves, 2.) TMSOTf / 1.) CH₂Cl₂, Et₂O, 1.5 h, 2.) CH₂Cl₂, Et₂O, 1,5 h

With methanol; trimethylsilyl trifluoromethanesulfonate; silver silicate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; In dichloromethane; toluene;

DOI:10.1016/0040-4020(95)01093-9

upstream raw materials:

[5-((2S,3R,4R,5S,6S)-3,4-Bis-benzyloxy-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid benzyl ester

5-<(benzyloxycarbonyl)amino>pentanol

ethyl 2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

ethyl 4-O-benzoyl-2,3-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

{5-[(2S,3R,4R,5S,6S)-3,4-Bis-benzyloxy-5-((2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-pentyl}-carbamic acid benzyl ester

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