(4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

• Chemical Name: (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS No.: 144985-29-5
• Molecular Formula: C₇₃H₇₆O₁₅
• Molecular Weight: 1193.4
• Mol file: 144985-29-5.mol

Synonyms:(4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chemical Property of (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 31 articles about (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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:

β-D-galactose peracetate (4163-60-4) → (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (144985-29-5)

Guidance literature:

Multi-step reaction with 7 steps

1: SnCl₄ / (CH₂Cl)2

2: NaOMe / methanol; tetrahydrofuran

3: 1) Bu₂SnO, 2) Bu₄NBr / 1) toluene, THF, reflux, 2) THF, reflux

4: TsOH*H₂O / tetrahydrofuran

6: 86 percent / CuBr₂, n-Bu₄NBr, AgOTf, MS₄A / various solvent(s)

With tetrabutylammomium bromide; sodium methylate; silver trifluoromethanesulfonate; tin(IV) chloride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; copper(ll) bromide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (144985-29-5)

Guidance literature:

Multi-step reaction with 12 steps

1: NaOMe / methanol; tetrahydrofuran

2: 1) Bu₂SnO, 2) Bu₄NBr / 1) THF, toluene, 2) THF

3: TsOH*H₂O / tetrahydrofuran

4: DMAP, pyridine

5: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

7: CCl₄, (Me₂N)3P / THF

8: 75 percent / silver triflate, MS₄A / CH₂Cl₂; toluene / -50 °C

9: 1) LiOH, 30percent H₂O₂, 2) KI, Ag₂O / 1) THF, 2) DMF

10: 1) H₂, 2) I₂, H₂O / 2MeP)2>PF₆ / 1) THF

11: 86 percent / CuBr₂, n-Bu₄NBr, AgOTf, MS₄A / various solvent(s)

With pyridine; hydrogenchloride; tetrachloromethane; dmap; lithium hydroxide; 4 A molecular sieve; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; copper(ll) bromide; silver(l) oxide; Hexamethylphosphorous triamide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside (144985-19-3) → (4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (144985-29-5)

Guidance literature:

Multi-step reaction with 10 steps

1: TsOH*H₂O / tetrahydrofuran

2: DMAP, pyridine

3: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

5: CCl₄, (Me₂N)3P / THF

6: 75 percent / silver triflate, MS₄A / CH₂Cl₂; toluene / -50 °C

7: 1) LiOH, 30percent H₂O₂, 2) KI, Ag₂O / 1) THF, 2) DMF

8: 1) H₂, 2) I₂, H₂O / 2MeP)2>PF₆ / 1) THF

9: 86 percent / CuBr₂, n-Bu₄NBr, AgOTf, MS₄A / various solvent(s)

With pyridine; hydrogenchloride; tetrachloromethane; dmap; lithium hydroxide; 4 A molecular sieve; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; iodine; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; copper(ll) bromide; silver(l) oxide; Hexamethylphosphorous triamide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)61200-5

upstream raw materials:

benzyl bromide

Acetic acid (4aR,6S,7R,8S,8aS)-8-allyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Methyl 3-O-allyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

C₁₀₂H₁₀₆O₂₅

Refernces

• 1、 Goto, Fumitaka,Ogawa, Tomoya. "SYNTHESIS OF SULFATED GLYCOHEXAOSE OF LINKAGE REGION OF CHONDROITIN 4-SULFATE: β-D-GlcA-(1->3)((SO3Na->4))-β-D-GalNAc-(1->4)-β-D-GlcA-(1->3)-β-D-Gal-(1->3)-β-D-Gal-(1->4)-D-Xyl". . p. 6841 - 6844. Retrieved 2007/10/02.