6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

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Chemical Name:6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one
CAS No.:365546-11-8
Molecular Formula:C₄₄H₄₂O₁₀
Molecular Weight:730.811
Hs Code.:

Synonyms:6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

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Chemical Property of 6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

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Technology Process of 6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

There total 16 articles about 6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one 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: 60.0%

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 282723-42-6
2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone

: 365546-11-8
6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

Guidance literature:: (furan-2-yloxy)-trimethylsilane; 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone; In chloroform; at 0 ℃; for 1h;

With silica gel; In methanol; acetonitrile; for 18h; Further stages.;
DOI:10.1039/b103080a

Reference yield:

: 481-39-0
5-hydroxynaphtho-1,4-quinone

: 365546-11-8
6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: 90 percent / Ag₂O / CHCl₃

2.1: aq. Na₂S₂O₄ / CH₂Cl₂; diethyl ether / 0.17 h

3.1: 3.33 g / K₂CO₃ / acetone / 48 h / Heating

4.1: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h

5.1: 73 percent / BF₃*Et₂O / acetonitrile / 0.33 h / 0 °C

6.1: NaH / dimethylformamide / 0.08 h / 0 °C

6.2: 85 percent / dimethylformamide / 12 h / 0 - 20 °C

7.1: 93 percent / aq. CAN / acetonitrile / 0.5 h

8.1: aq. Na₂S₂O₄ / CH₂Cl₂; diethyl ether / 0.17 h

9.1: 643 mg / K₂CO₃ / acetone / Heating

10.1: 77 percent / Br₂ / CCl₄ / 0.03 h / 0 °C

11.1: 84 percent / aq. NaOH / dimethylformamide / 0.5 h / 20 °C

12.1: Pd(PPh₃)2Cl₂ / toluene / 18 h / 100 °C

13.1: 95 mg / aq. HCl / toluene; CH₂Cl₂ / 0.5 h

14.1: 93 percent / AgO; HNO₃ / dioxane / 0.33 h

15.1: CHCl₃ / 1 h / 0 °C

15.2: 60 percent / silica gel / acetonitrile; methanol / 18 h

With hydrogenchloride; silver(II) oxide; sodium hydroxide; sodium dithionite; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen; bromine; nitric acid; sodium hydride; potassium carbonate; silver(l) oxide; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 12.1: Stille coupling;
DOI:10.1039/b103080a

Reference yield:

: 91963-30-3
5,8-dimethoxynaphthalen-1-ol

: 365546-11-8
6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 73 percent / BF₃*Et₂O / acetonitrile / 0.33 h / 0 °C

2.1: NaH / dimethylformamide / 0.08 h / 0 °C

2.2: 85 percent / dimethylformamide / 12 h / 0 - 20 °C

3.1: 93 percent / aq. CAN / acetonitrile / 0.5 h

4.1: aq. Na₂S₂O₄ / CH₂Cl₂; diethyl ether / 0.17 h

5.1: 643 mg / K₂CO₃ / acetone / Heating

6.1: 77 percent / Br₂ / CCl₄ / 0.03 h / 0 °C

7.1: 84 percent / aq. NaOH / dimethylformamide / 0.5 h / 20 °C

8.1: Pd(PPh₃)2Cl₂ / toluene / 18 h / 100 °C

9.1: 95 mg / aq. HCl / toluene; CH₂Cl₂ / 0.5 h

10.1: 93 percent / AgO; HNO₃ / dioxane / 0.33 h

11.1: CHCl₃ / 1 h / 0 °C

11.2: 60 percent / silica gel / acetonitrile; methanol / 18 h

With hydrogenchloride; silver(II) oxide; sodium hydroxide; sodium dithionite; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; bromine; nitric acid; sodium hydride; potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8.1: Stille coupling;
DOI:10.1039/b103080a