4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester
• CAS No.: 351885-01-3
• Molecular Formula: C₂₁H₂₁NO₉
• Molecular Weight: 431.399

Synonyms:4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester

Chemical Property of 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester

There total 3 articles about 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-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: 95.0%

4-Nitro-benzoic acid (1R,2R,5S,7R)-7-benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-yl ester (351885-00-2) → 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester (351885-01-3)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water;

DOI:10.1021/ol015963x

Reference yield:

(1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester (351885-01-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaBH₄; CeCl₃ / 0 °C

2: PPh₃; DIAD / tetrahydrofuran

3: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1021/ol015963x

Reference yield:

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol (243987-96-4) → 4-Nitro-benzoic acid (1S,2R,3R,4S,5S,7R)-7-benzyloxymethyl-3,4-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester (351885-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: PPh₃; DIAD / tetrahydrofuran

2: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O

With osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1021/ol015963x

upstream raw materials:

4-Nitro-benzoic acid (1R,2R,5S,7R)-7-benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-yl ester

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol

Downstream raw materials:

(1S,2R,3S,4S,5S,7R)-7-Benzyloxymethyl-2,3,4-tris-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]octane

(1S,4R,5R,6S)-4,5,6-Tris-methoxymethoxy-cyclohex-2-enol

conduritol D

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