Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester
• CAS No.: 909782-03-2
• Molecular Formula: C₄₃H₄₆O₁₁
• Molecular Weight: 738.832

Synonyms:Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester

There total 5 articles about Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-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: 96.0%

Benzoic acid (R)-4-[(2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,3-dioxo-butyl ester (909782-01-0) → Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester (909782-03-2)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (909781-96-0) → Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester (909782-03-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / -80 °C

1.2: 73 percent / tetrahydrofuran / -80 - -20 °C

2.1: 96 percent / DMAP; pyridine

3.1: 73 percent / RuO₂; NaIO₄ / CCl₄; acetonitrile; H₂O

4.1: 96 percent / CSA / methanol; CH₂Cl₂

With pyridine; dmap; ruthenium(IV) oxide; sodium periodate; n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

(S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol (909781-97-1) → Benzoic acid (2R,3R,4S,4aS,5aS,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-5a,11a-dihydroxy-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester (909782-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / DMAP; pyridine

2: 73 percent / RuO₂; NaIO₄ / CCl₄; acetonitrile; H₂O

3: 96 percent / CSA / methanol; CH₂Cl₂

With pyridine; dmap; ruthenium(IV) oxide; sodium periodate; camphor-10-sulfonic acid; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

upstream raw materials:

Benzoic acid (R)-4-[(2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2,3-dioxo-butyl ester

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

(S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

Benzoic acid (S)-4-[(2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl ester

Downstream raw materials:

C₆₂H₇₀N₆O₁₆

(2R,4aR,5aS,6aR,7aS,11aS,12R,12aR,13aS,14R,14aR)-12,14-Bis-allyloxy-2-phenyl-tetradecahydro-1,3,5,7,11,13-hexaoxa-pentacene

(2R,4aR,5aS,6aR,7aS,11aR,12R,12aS,13aR,14R,14aS)-2-Phenyl-tetradecahydro-1,3,5,7,11,13-hexaoxa-pentacene-12,14-diol

Benzoic acid (2R,3R,4S,4aS,5aR,6R,6aS,10aS,11aR,12aS)-3,4-bis-benzyloxy-2-benzyloxymethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-6-yl ester

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