Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester
CAS No.:1054622-92-2
Molecular Formula:C₅₆H₆₈O₁₃Si
Molecular Weight:977.234
Hs Code.:

Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

There total 11 articles about Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-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:

: 756496-82-9
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(p-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-(thexyldimethylsilyl)-β-D-glucopyranoside

: 1054622-92-2
Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: With sodium acetate; palladium dichloride; In water; acetic acid; for 24h;
DOI:10.1002/ejoc.200300807

Reference yield:

: 100-39-0
benzyl bromide

: 1054622-92-2
Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 630 mg / NaH / dimethylformamide / 5 h

2: nBu₄NF / tetrahydrofuran / -30 - 20 °C

3: 0.99 g / imidazole / dimethylformamide / 4 h / 0 °C

4: 50 percent / Et₃N / acetonitrile / 24 h / -40 °C

5: 51 percent / NaH; KI / dimethylformamide / 5 h / -30 °C

6: PdCl₂; NaOAc / acetic acid; H₂O / 24 h

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; triethylamine; potassium iodide; palladium dichloride; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200300807

Reference yield:

: 299174-87-1
2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

: 1054622-92-2
Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaOMe; MeOH / 4 h

2.1: Bu₂SnO / methanol / 15 h / 60 °C

2.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

3.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

4.1: camphorsulfonic acid / acetonitrile / 0.5 h

5.1: 3.35 g / collidine / dimethylformamide / 20 °C

6.1: NaOH / ethanol / 40 °C

7.1: 630 mg / NaH / dimethylformamide / 5 h

8.1: nBu₄NF / tetrahydrofuran / -30 - 20 °C

9.1: 0.99 g / imidazole / dimethylformamide / 4 h / 0 °C

10.1: 50 percent / Et₃N / acetonitrile / 24 h / -40 °C

11.1: 51 percent / NaH; KI / dimethylformamide / 5 h / -30 °C

12.1: PdCl₂; NaOAc / acetic acid; H₂O / 24 h

With 1H-imidazole; 2,3,5-trimethyl-pyridine; methanol; sodium hydroxide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; sodium hydride; di(n-butyl)tin oxide; triethylamine; potassium iodide; palladium dichloride; In tetrahydrofuran; methanol; ethanol; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Zemplen deacetylation;
DOI:10.1002/ejoc.200300807