((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester

Base Information

• Chemical Name: ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester
• CAS No.: 182418-29-7
• Molecular Formula: C₂₈H₄₃F₃O₁₀S
• Molecular Weight: 628.705

Synonyms:

Chemical Property of ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester

There total 14 articles about ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl 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:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester (182418-29-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 85 percent / NaBH₄ / tetrahydrofuran

2: NaH

3: 1) H⁽¹⁺⁾, 2) pyridine

4: 1) TiBr₄, 2) HgO, HgBr, CaSO₄ / 1) CHCl₃

5: NaOMe, MeOH

6: pTSA / acetonitrile

7: NaH / tetrahydrofuran

8: NaOAc, benzene sulphonylhydrazide / 1,2-dimethoxy-ethane; H₂O

9: I₂, MeOH

10: pyridine / Heating

11: NaH, DMF

12: acidic ion-exchange resin / methanol

13: pyridine / CH₂Cl₂

With pyridine; methanol; calcium sulfate; sodium tetrahydroborate; acidic ion-exchange resin; iodine; sodium methylate; sodium acetate; mercury(I) bromide; hydrogen cation; titanium(IV) bromide; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; benzenesufonyl hydrazide; mercury(II) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;

DOI:10.1016/0960-894X(96)00336-8

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester (182418-29-7)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH

2: 1) H⁽¹⁺⁾, 2) pyridine

3: 1) TiBr₄, 2) HgO, HgBr, CaSO₄ / 1) CHCl₃

4: NaOMe, MeOH

5: pTSA / acetonitrile

6: NaH / tetrahydrofuran

7: NaOAc, benzene sulphonylhydrazide / 1,2-dimethoxy-ethane; H₂O

8: I₂, MeOH

9: pyridine / Heating

10: NaH, DMF

11: acidic ion-exchange resin / methanol

12: pyridine / CH₂Cl₂

With pyridine; methanol; calcium sulfate; acidic ion-exchange resin; iodine; sodium methylate; sodium acetate; mercury(I) bromide; hydrogen cation; titanium(IV) bromide; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; benzenesufonyl hydrazide; mercury(II) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;

DOI:10.1016/0960-894X(96)00336-8

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose (22331-21-1) → ((2R,3R,4R,5R,6R)-4-Benzyloxy-5,6-diisobutoxy-2-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester (182418-29-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) H⁽¹⁺⁾, 2) pyridine

2: 1) TiBr₄, 2) HgO, HgBr, CaSO₄ / 1) CHCl₃

3: NaOMe, MeOH

4: pTSA / acetonitrile

5: NaH / tetrahydrofuran

6: NaOAc, benzene sulphonylhydrazide / 1,2-dimethoxy-ethane; H₂O

7: I₂, MeOH

8: pyridine / Heating

9: NaH, DMF

10: acidic ion-exchange resin / methanol

11: pyridine / CH₂Cl₂

With pyridine; methanol; calcium sulfate; acidic ion-exchange resin; iodine; sodium methylate; sodium acetate; mercury(I) bromide; hydrogen cation; titanium(IV) bromide; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; benzenesufonyl hydrazide; mercury(II) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetonitrile;

DOI:10.1016/0960-894X(96)00336-8

upstream raw materials:

trifluoromethylsulfonic anhydride

((2R,3R,4R,5R,6R)-4-Benzyloxy-2-hydroxymethyl-5,6-diisobutoxy-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

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