4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester
• CAS No.: 106974-28-1
• Molecular Formula: C₅₅H₅₅NO₁₃
• Molecular Weight: 938.041

Synonyms:4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

Chemical Property of 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

There total 9 articles about 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-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: 22.0%

4-nitro-benzoyl chloride (122-04-3) + (3S,4R,5R,6R)-3,4-Bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ol → 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester (106974-28-1) + 4-Nitro-benzoic acid (2S,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester (106929-16-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo00028a017

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester (106974-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH / 1) THF, 0 deg C, 30 min., 2) r.t., 1.5 h

2: 80 percent / 60percent CH₃COOH / H₂O / 20 h / 40 °C

3: 98 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

4: 70 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; lead(IV) acetate; sodium hydride; acetic acid; In dichloromethane; water; benzene;

DOI:10.1021/jo00028a017

Reference yield:

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol (106929-11-7) → 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester (106974-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH / 1) THF, 0 deg C, 30 min., 2) r.t., 1.5 h

2: 80 percent / 60percent CH₃COOH / H₂O / 20 h / 40 °C

3: 98 percent / Pb(OAc)4 / benzene / 0.17 h / 0 °C

4: 70 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; lead(IV) acetate; sodium hydride; acetic acid; In dichloromethane; water; benzene;

DOI:10.1021/jo00028a017

upstream raw materials:

4-nitro-benzoyl chloride

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-ol

p-Methoxybenzyl bromide

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

Downstream raw materials:

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol

Benzoic acid (2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Benzoic acid (2R,3R,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester

(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-hydroxymethyl-tetrahydro-pyran-3-ol

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